METHOD FOR PREPARING DEUTERATED CHEMICAL BY MEANS OF DEUTERATION REACTION OF CARBON-HYDROGEN BOND WITH DEUTERIUM GAS UNDER CATALYSIS OF ALKALI

Abstract

The present application provides a method for preparing a deuterated chemical by means of a deuteration reaction of a carbon-hydrogen bond with a deuterium gas under the catalysis of an alkali, wherein in the presence of a catalyst, a deuterium gas is added into a compound containing a carbon-hydrogen bond for a deuteration reaction so as to generate a deuterated compound. A deuterium gas is used as a deuterium source, such that multiple water separation operations, tedious steps and the wasting of energy caused by usage of a large amount of deuterium oxide as a deuterium source are avoided. Moreover, a cheap and easily available alkali metal compound is used for replacing an expensive transition metal catalyst and a complex-structure ligand as a catalyst for a deuteration reaction, and the alkali metal compound has the advantages of a low cost, a good compatibility with functional groups of a substrate and a high deuteration rate. The present application provides a new, low-cost, green and efficient deuteration method, which has a high application value.

Claims

1. A method for deuteration of a carbon-hydrogen bond, comprising the following steps: in the presence of a catalyst, introducing deuterium gas into a compound containing carbon-hydrogen bonds for deuteration to produce deuterated compounds; wherein, said catalyst is selected from at least one of alkali metal hydroxides, alkali metal alkoxides, alkali metal hydrides, alkali metal hydrocarbon compounds, and alkali metal amino compounds.

2. The method of claim 1, wherein, said alkali metal hydroxide is selected from at least one of lithium hydroxide, sodium hydroxide, potassium hydroxide, rubidium hydroxide, and cesium hydroxide; said alkali metal alkoxide is selected from at least one of lithium methoxide, lithium ethoxide, lithium isopropoxide, lithium tert-butoxide, sodium methoxide, sodium ethoxide, sodium isopropoxide, sodium tert-butoxide, potassium methoxide, potassium ethoxide, potassium isopropoxide, potassium tert-butoxide, alkoxyl rubidium, and alkoxyl cesium; said alkoxyl rubidium is selected from at least one of rubidium methoxide, rubidium ethoxide, rubidium isopropoxide, and rubidium tert-butoxide; said alkoxyl cesium is selected from at least one of cesium methoxide, cesium ethoxide, cesium isopropoxide, and cesium tert-butoxide; said alkali metal hydride is selected from at least one of lithium hydride, sodium hydride, potassium hydride, rubidium hydride, and cesium hydride; said alkali metal hydrocarbon compound is selected from at least one of methyl lithium, trimethylsilylmethyl lithium, ethyl lithium, n-butyl lithium, sec-butyl lithium, tert-butyl lithium, benzyl lithium, phenyl lithium, benzyl sodium, benzyl potassium, benzyl rubidium, and benzyl cesium; said alkali metal amino compound is selected from at least one of lithium amide, lithium dimethylamide, lithium diethylamide, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, lithium tetramethylpiperidide, sodium amide, sodium diisopropylamide, sodium bis(trimethylsilyl)amide, potassium amide, potassium dimethylamide, potassium diethylamide, potassium diisopropylamide, potassium bis(trimethylsilyl)amide, potassium tetramethylpiperidide, rubidium dimethylamide, rubidium diethylamide, rubidium diisopropylamide, rubidium bis(trimethylsilyl)amide, rubidium tetramethylpiperidide, cesium dimethylamide, cesium diethylamide, cesium diisopropylamide, cesium bis(trimethylsilyl)amide, and cesium tetramethylpiperidide.

3. The method of claim 2, wherein, said alkali metal amino compound is synthesized in situ using an alkali metal hydrocarbon compound and an amine, or using lithium amide and an alkali metal salt; said alkali metal amino compound is selected from at least one of sodium diisopropylamide, potassium dimethylamide, potassium diethylamide, potassium diisopropylamide, potassium bis(trimethylsilyl)amide, potassium tetramethylpiperidide, rubidium dimethylamide, rubidium diethylamide, rubidium diisopropylamide, rubidium bis(trimethylsilyl)amide, rubidium tetramethylpiperidide, cesium dimethylamide, cesium diethylamide, cesium diisopropylamide, cesium bis(trimethylsilyl)amide, and cesium tetramethylpiperidide; wherein, said alkali metal hydrocarbon compound is selected from at least one of butyl lithium, benzyl potassium, benzyl rubidium, and benzyl cesium; said amine is selected from at least one of dimethylamine, diethylamine, diisopropylamine, bis(trimethylsilyl)amine, and tetramethylpiperidide; said lithium amide is selected from at least one of lithium dimethylamide, lithium diethylamide, lithium diisopropylamide, lithium bis(trimethylsilyl)amide, and lithium tetramethylpiperidide; said alkali metal salt is selected from at least one of sodium salts, potassium salts, rubidium salts, and cesium salts; said sodium salt is selected from sodium hydride, sodium tert-butoxide; said potassium salt is selected from potassium hydride, potassium tert-butoxide; said rubidium salt is selected from at least one of rubidium fluoride, rubidium chloride, rubidium bromide, rubidium iodide, rubidium nitrate, rubidium sulfate, rubidium carbonate, rubidium formate, rubidium acetate, and rubidium perchlorate; said cesium salt is selected from at least one of cesium fluoride, cesium chloride, cesium bromide, cesium iodide, cesium nitrate, cesium sulfate, cesium carbonate, cesium formate, cesium acetate, and cesium perchlorate.

4. The method of claim 3, wherein, said compound containing a carbon-hydrogen bond is selected from at least one of the following: aromatic compounds with carbon-hydrogen bonds at the benzyl position; thioether compounds with carbon-hydrogen bonds at the position; sulfone, sulfoxide, sulfonamide, and sulfinamide compounds with carbon-hydrogen bonds at the position; aryl ether compounds, fluorobenzene compounds, aromatic hydrocarbons, heteroaromatic hydrocarbons with aromatic carbon-hydrogen bonds; and alkene compounds with alkenyl carbon-hydrogen bonds.

5. The method of claim 1, wherein, said deuteration reaction is shown in any one of Reaction Equation 1 to Reaction Equation 5; Reaction Equation 1 is: ##STR00053## Reaction Equation 2 is: ##STR00054## R.sub.1 to R.sub.5 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, C.sub.3-C.sub.9 silyl group, and C.sub.1-C.sub.20 amino group, two adjacent groups in R.sub.1-R.sub.3 can be connected into a ring, X.sub.1 is a carbon atom or a nitrogen atom, and X.sub.2 is an oxygen atom, a sulfur atom, or a nitrogen atom; Reaction Equation 3 is: ##STR00055## Reaction Equation 4 is: ##STR00056## R.sub.6 to R.sub.10 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, or C.sub.1-C.sub.20 amino group, two adjacent groups in R.sub.6-R.sub.8 can be connected into a ring, X.sub.2 is an oxygen atom, a sulfur atom, or a nitrogen atom, and X.sub.3 is selected from any one of a silicon atom, an oxygen atom, a sulfur atom, a carbon atom, or a nitrogen atom; R is a C.sub.1-C.sub.10 hydrocarbon group or a C.sub.6-C.sub.20 aryl group; Reaction Equation 5 is: ##STR00057## R.sub.11 to R.sub.20 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, or C.sub.1-C.sub.20 amino group.

6. The method of claim 1, wherein, said deuteration reaction is as shown in any one of Reaction Equation 6 to Reaction Equation 7: Reaction Equation 6 is: ##STR00058## R.sub.21 to R.sub.23 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, C.sub.3-C.sub.9 silyl group, C.sub.1-C.sub.10 alkoxyl group, or C.sub.1-C.sub.20 amino group, R.sub.21 to R.sub.23 can be connected into aliphatic hydrocarbon rings or aromatic rings; Reaction Equation 7 is: ##STR00059## R.sub.24 to R.sub.28 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, C.sub.1-C.sub.10 hydrocarbon sulfur group, or C.sub.1-C.sub.20 amino group, X.sub.4 is a carbon or nitrogen atom.

7. The method of claim 5, wherein, said catalyst is selected from at least one of potassium diisopropylamide, potassium bis(trimethylsilyl)amide, potassium tetramethylpiperidide, rubidium diisopropylamide, rubidium bis(trimethylsilyl)amide, rubidium tetramethylpiperidide, cesium diisopropylamide, cesium bis(trimethylsilyl)amide, and cesium tetramethylpiperidide.

8. The method of claim 1, wherein, said deuteration reaction is as shown in any one of Reaction Equation 8 to Reaction Equation 12; Reaction Equation 8 is: ##STR00060## Reaction Equation 9 is: ##STR00061## Reaction Equation 10 is: ##STR00062## Reaction Equation 11 is: ##STR00063## Reaction Equation 12 is: ##STR00064## R.sub.29 is independently selected from any one of C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, C.sub.1-C.sub.10 alkyloxyl group, or C.sub.1-C.sub.20 amino group, R.sub.30 is independently selected from any one of C.sub.1-C.sub.10 hydrocarbon group or C.sub.6-C.sub.20 aryl group, and R.sub.29, R.sub.30 can be connected into a ring; R.sub.31 to R.sub.34 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, C.sub.1-C.sub.10 alkyloxyl group, or C.sub.1-C.sub.20 amino group, and two adjacent groups among R.sub.31 to R.sub.34 can be connected into a ring.

9. The method of claim 8, wherein, said catalyst is selected from at least one of potassium tert-butoxide, sodium hydroxide, or potassium hydroxide.

10. The method of claim 1, wherein, said deuteration reaction is as shown in any one of Reaction Equations 13 to 15; Reaction Equation 13 is: ##STR00065## Reaction Equation 14 is: ##STR00066## Reaction Equation 15 is: ##STR00067## R.sub.35 to R.sub.40 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, or C.sub.6-C.sub.20 aryl group, and two adjacent groups among R.sub.35 to R.sub.40 can be connected into a ring.

11. The method of claim 1, wherein, said deuteration reaction is as shown in any one of Reaction Equation 16 to Reaction Equation 17; Reaction Equation 16 is: ##STR00068## Reaction Equation 17 is: ##STR00069## R.sub.36 to R.sub.38 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, or C.sub.6-C.sub.20 aryl group, and two adjacent groups among R.sub.36 to R.sub.38 can be connected into a ring, X.sub.5 is selected from any one of a silicon atom, an oxygen atom, a sulfur atom, a carbon atom, or a nitrogen atom.

12. According to claim 1, wherein, said deuteration reaction is as shown in Reaction Equation 18: Reaction Equation 18 is: ##STR00070## R.sub.41 and R.sub.42 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, C.sub.3-C.sub.9 silyl group, C.sub.1-C.sub.10 alkoxyl group, or C.sub.1-C.sub.20 amino group, and R.sub.41 and R.sub.42 can be connected into an aliphatic hydrocarbon ring or an aromatic ring.

13. The method of claim 10, wherein, said catalyst is selected from at least one of potassium diisopropylamide, potassium bis(trimethylsilyl)amide, potassium tetramethylpiperidide, rubidium diisopropylamide, rubidium bis(trimethylsilyl)amide, rubidium tetramethylpiperidide, cesium diisopropylamide, cesium bis(trimethylsilyl)amide, and cesium tetramethylpiperidide.

14. The method of claim 1, wherein, the molar amount of said catalyst is 1%-100% of the molar amount of said compound containing carbon-hydrogen bonds.

15. The method of claim 1, wherein, the pressure of deuterium gas in said deuteration reaction is between 1 bar-50 bar.

16. The method of claim 1, wherein, said deuteration reaction is conducted in an organic solvent or under solvent-free conditions, and said organic solvent is selected from at least one of deuterated benzene, benzene, tert-butylbenzene, n-hexane, cyclohexane, decalin, ether, tetrahydrofuran, methyl tert-butyl ether, methyl cyclopentyl ether, and n-butyl ether.

17. The method of claim 2, wherein, said deuteration reaction is shown in any one of Reaction Equation 1 to Reaction Equation 5; Reaction Equation 1 is: ##STR00071## Reaction Equation 2 is: ##STR00072## R.sub.1 to R.sub.5 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, C.sub.3-C.sub.9 silyl group, and C.sub.1-C.sub.20 amino group, two adjacent groups in R.sub.1-R.sub.3 can be connected into a ring, X.sub.1 is a carbon atom or a nitrogen atom, and X.sub.2 is an oxygen atom, a sulfur atom, or a nitrogen atom; Reaction Equation 3 is: ##STR00073## Reaction Equation 4 is: ##STR00074## R.sub.6 to R.sub.10 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, or C.sub.1-C.sub.20 amino group, two adjacent groups in R.sub.6-R.sub.8 can be connected into a ring, X.sub.2 is an oxygen atom, a sulfur atom, or a nitrogen atom, and X.sub.3 is selected from any one of a silicon atom, an oxygen atom, a sulfur atom, a carbon atom, or a nitrogen atom; R is a C.sub.1-C.sub.10 hydrocarbon group or a C.sub.6-C.sub.20 aryl group; Reaction Equation 5 is: ##STR00075## R.sub.11 to R.sub.20 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, or C.sub.1-C.sub.20 amino group.

18. The method of claim 3, wherein, said deuteration reaction is shown in any one of Reaction Equation 1 to Reaction Equation 5; Reaction Equation 1 is: ##STR00076## Reaction Equation 2 is: ##STR00077## R.sub.1 to R.sub.5 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, C.sub.3-C.sub.9 silyl group, and C.sub.1-C.sub.20 amino group, two adjacent groups in R.sub.1-R.sub.3 can be connected into a ring, X.sub.1 is a carbon atom or a nitrogen atom, and X.sub.2 is an oxygen atom, a sulfur atom, or a nitrogen atom; Reaction Equation 3 is: ##STR00078## Reaction Equation 4 is: ##STR00079## R.sub.6 to R.sub.10 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, or C.sub.1-C.sub.20 amino group, two adjacent groups in R.sub.6-R.sub.8 can be connected into a ring, X.sub.2 is an oxygen atom, a sulfur atom, or a nitrogen atom, and X.sub.3 is selected from any one of a silicon atom, an oxygen atom, a sulfur atom, a carbon atom, or a nitrogen atom; R is a C.sub.1-C.sub.10 hydrocarbon group or a C.sub.6-C.sub.20 aryl group; Reaction Equation 5 is: ##STR00080## R.sub.11 to R.sub.20 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, or C.sub.1-C.sub.20 amino group.

19. The method of claim 4, wherein, said deuteration reaction is shown in any one of Reaction Equation 1 to Reaction Equation 5; Reaction Equation 1 is: ##STR00081## Reaction Equation 2 is: ##STR00082## R.sub.1 to R.sub.5 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, C.sub.3-C.sub.9 silyl group, and C.sub.1-C.sub.20 amino group, two adjacent groups in R.sub.1-R.sub.3 can be connected into a ring, X.sub.1 is a carbon atom or a nitrogen atom, and X.sub.2 is an oxygen atom, a sulfur atom, or a nitrogen atom; Reaction Equation 3 is: ##STR00083## Reaction Equation 4 is: ##STR00084## R.sub.6 to R.sub.10 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, or C.sub.1-C.sub.20 amino group, two adjacent groups in R.sub.6-R.sub.8 can be connected into a ring, X.sub.2 is an oxygen atom, a sulfur atom, or a nitrogen atom, and X.sub.3 is selected from any one of a silicon atom, an oxygen atom, a sulfur atom, a carbon atom, or a nitrogen atom; R is a C.sub.1-C.sub.10 hydrocarbon group or a C.sub.6-C.sub.20 aryl group; Reaction Equation 5 is: ##STR00085## R.sub.11 to R.sub.20 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, or C.sub.1-C.sub.2M amino group.

20. The method of claim 2, wherein, said deuteration reaction is as shown in any one of Reaction Equation 6 to Reaction Equation 7: Reaction Equation 6 is: ##STR00086## R.sub.21 to R.sub.23 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, C.sub.3-C.sub.9 silyl group, C.sub.1-C.sub.10 alkoxyl group, or C.sub.1-C.sub.2M amino group, R.sub.21 to R.sub.23 can be connected into aliphatic hydrocarbon rings or aromatic rings; Reaction Equation 7 is: ##STR00087## R.sub.24 to R.sub.28 are independently selected from any one of H, C.sub.1-C.sub.10 hydrocarbon group, C.sub.6-C.sub.20 aryl group, halogen, C.sub.1-C.sub.10 hydrocarboxyl group, C.sub.1-C.sub.10 hydrocarbon sulfur group, or C.sub.1-C.sub.20 amino group, X.sub.4 is a carbon or nitrogen atom.

Description

DESCRIPTION OF DRAWINGS

[0095] In order to provide a clearer understanding of the technical solutions in the embodiments of this application, a brief introduction to the drawings required for the embodiments is presented below. It is evident that the following descriptions of the drawings are only some of the embodiments of this application, and those skilled in the art can obtain additional drawings based on these.

[0096] FIG. 1 is the .sup.1H NMR spectrum of deuterated 4-phenyltoluene in Example 6;

[0097] FIG. 2 is the .sup.13C NMR spectrum of deuterated 4-phenyltoluene in Example 6;

[0098] FIG. 3 is the .sup.1H NMR spectrum of deuterated p-xylene in Example 21;

[0099] FIG. 4 is the .sup.13C NMR spectrum of deuterated p-xylene in Example 21;

[0100] FIG. 5 is the .sup.1H NMR spectrum of deuterated 4-ethylbiphenyl in Example 22;

[0101] FIG. 6 is the .sup.13C NMR spectrum of deuterated 4-ethylbiphenyl in Example 22;

[0102] FIG. 7 is the .sup.1H NMR spectrum of deuterated 2-methylpyridine in Example 23;

[0103] FIG. 8 is the .sup.13C NMR spectrum of deuterated 2-methylpyridine in Example 23;

[0104] FIG. 9 is the .sup.1H NMR spectrum of deuterated 3-methylpyridine in Example 24;

[0105] FIG. 10 is the .sup.13C NMR spectrum of deuterated 3-methylpyridine in Example 24;

[0106] FIG. 11 is the .sup.1H NMR spectrum of deuterated 1,2-dimethylindole in Example 25;

[0107] FIG. 12 is the .sup.13C NMR spectrum of deuterated 1,2-dimethylindole in Example 25;

[0108] FIG. 13 is the .sup.1H NMR spectrum of deuterated 2-methylbenzothiophene in Example 26;

[0109] FIG. 14 is the .sup.13C NMR spectrum of deuterated 2-methylbenzothiophene in Example 26;

[0110] FIG. 15 is the .sup.1H NMR spectrum of deuterated diphenylmethane in Example 27;

[0111] FIG. 16 is the .sup.13C NMR spectrum of deuterated diphenylmethane in Example 27;

[0112] FIG. 17 is the .sup.1H NMR spectrum of deuterated benzylmethyl ether in Example 28;

[0113] FIG. 18 is the .sup.13C NMR spectrum of deuterated benzylmethyl ether in Example 28;

[0114] FIG. 19 is the .sup.1H NMR spectrum of deuterated benzyl phenyl sulfide in Example 29;

[0115] FIG. 20 is the .sup.13C NMR spectrum of deuterated benzyl phenyl sulfide in Example 29;

[0116] FIG. 21 is the .sup.1H NMR spectrum of deuterated N-ethyl-N-benzyl aniline in Example 30;

[0117] FIG. 22 is the .sup.13C NMR spectrum of deuterated N-ethyl-N-benzyl aniline in Example 30;

[0118] FIG. 23 is the .sup.1H NMR spectrum of deuterated phenyl methyl sulfide in Example 31;

[0119] FIG. 24 is the .sup.13C NMR spectrum of deuterated phenyl methyl sulfide in Example 31;

[0120] FIG. 25 is the .sup.1H NMR spectrum of deuterated methylthiocyclohexyl ester in Example 32;

[0121] FIG. 26 is the .sup.13C NMR spectrum of deuterated methylthiocyclohexyl ester in Example 32;

[0122] FIG. 27 is the .sup.1H NMR spectrum of deuterated dimethyl sulfoxide in Example 33;

[0123] FIG. 28 is the .sup.13C NMR spectrum of deuterated dimethyl sulfoxide in Example 33;

[0124] FIG. 29 is the .sup.1H NMR spectrum of deuterated phenyl methyl sulfoxide in Example 34;

[0125] FIG. 30 is the .sup.13C NMR spectrum of deuterated phenyl methyl sulfoxide in Example 34;

[0126] FIG. 31 is the .sup.1H NMR spectrum of deuterated N,N-dimethylmethanesulfonamide in Example 35;

[0127] FIG. 32 is the .sup.13C NMR spectrum of deuterated N,N-dimethylmethanesulfonamide in Example 35;

[0128] FIG. 33 is the .sup.1H NMR spectrum of deuterated anisole in Example 36;

[0129] FIG. 34 is the .sup.13C NMR spectrum of deuterated anisole in Example 36;

[0130] FIG. 35 is the .sup.1H NMR spectrum of deuterated 1,3-benzodioxole in Example 37;

[0131] FIG. 36 is the .sup.13C NMR spectrum of deuterated 1,3-benzodioxole in Example 37;

[0132] FIG. 37 is the .sup.1H NMR spectrum of deuterated 4-fluorobiphenyl in Example 38;

[0133] FIG. 38 is the .sup.13C NMR spectrum of deuterated 4-fluorobiphenyl in Example 38;

[0134] FIG. 39 is the .sup.1H NMR spectrum of deuterated 1,4-difluorobenzene in Example 39;

[0135] FIG. 40 is the .sup.13C NMR spectrum of deuterated 1,4-difluorobenzene in Example 39;

[0136] FIG. 41 is the .sup.1H NMR spectrum of deuterated benzene in Example 40;

[0137] FIG. 42 is the .sup.13C NMR spectrum of deuterated benzene in Example 40;

[0138] FIG. 43 is the .sup.1H NMR spectrum of deuterated pyridine in Example 45;

[0139] FIG. 44 is the .sup.13C NMR spectrum of deuterated pyridine in Example 45;

[0140] FIG. 45 is the .sup.1H NMR spectrum of deuterated 2-phenylpyridine in Example 46;

[0141] FIG. 46 is the .sup.13C NMR spectrum of deuterated 2-phenylpyridine in Example 46;

[0142] FIG. 47 is the .sup.1H NMR spectrum of deuterated 2,2-bipyridine in Example 47;

[0143] FIG. 48 is the .sup.1H NMR spectrum of deuterated N-methylindole in Example 48;

[0144] FIG. 49 is the .sup.13C NMR spectrum of deuterated N-methylindole in Example 48;

[0145] FIG. 50 is the .sup.1H NMR spectrum of deuterated benzothiophene in Example 49;

[0146] FIG. 51 is the .sup.13C NMR spectrum of deuterated benzothiophene in Example 49;

[0147] FIG. 52 is the .sup.1H NMR spectrum of deuterated P-methylstyrene in Example 50;

[0148] FIG. 53 is the .sup.1H NMR spectrum of deuterated 2,3-dihydrofuran in Example 51;

[0149] FIG. 54 is the .sup.1H NMR spectrum of deuterated 1,4-dioxene in Example 52;

[0150] FIG. 55 is the .sup.1H NMR spectrum of deuterated 1,3-bis-(2,4,6-trimethylphenyl)imidazol-2-ylidene in Example 53.

PREFERRED EMBODIMENTS OF THE INVENTION

[0151] In order to make the objectives, technical solutions, and advantages of the present application clearer and more understandable, specific embodiments are described below with reference to the attached drawings for further illustrating the present application. Obviously, the described embodiments are only part of the embodiments of the present application, not all of them. All other embodiments obtained by those skilled in the art based on the embodiments in the present application are within the scope of protection of the present application.

EXAMPLES

[0152] Below, examples are provided to further illustrate the embodiments of the present application. The chemical structures of deuterated products in the deuteration reactions of the embodiments show the positions of deuterated carbon-hydrogen bonds and the corresponding deuteration rate.

[0153] The following abbreviations are used in the examples:

TABLE-US-00001 TABLE 1 Full name Abbreviation Full name Abbreviation Lithium LiHMDS Potassium KO.sup.tBu bis(trimethylsilyl)amide tert-butoxide Sodium NaHMDS Potassium KH bis(trimethylsilyl)amide hydride Potassium KHMDS Cesium fluoride CsF bis(trimethylsilyl)amide Cesium CsHMDS Rubidium RbF bis(trimethylsilyl)amide fluoride Benzyl potassium BnK Cesium carbonate Cs.sub.2CO.sub.3 Methyl tert-Butyl ether TBME Deuterium D.sub.2 Benzene-d.sub.6 C.sub.6D.sub.6

[0154] The preparation of the cesium bis(trimethylsilyl)amide (CsHMDS) catalyst used in the following examples includes:

[0155] Under an inert atmosphere, 10 mmol of lithium bis(trimethylsilyl)amide (LiHMDS), 10 mmol of cesium fluoride (CsF), and 30 mL of dry n-hexane were added to a reaction flask equipped with a magnetic stirrer. The reaction solution was heated and refluxed for 15 hours. After the reaction was completed, the solvent was evaporated. Then, 30 mL of toluene was added to dissolve cesium bis(trimethylsilyl)amide (CsHMDS), filtered, and the solvent was drained to obtain 2.20 g of white solid, with a yield of 75%.

[0156] The preparation of the benzyl potassium (BnK) catalyst used in the following examples includes: [0157] At 78 C., 21 mL of n-butyl lithium (.sup.nBuLi, molar concentration 2.4 M) in hexane was slowly added to a suspension of 100 mL of potassium tert-butoxide (KO.sup.tBu, molar quantity 50 mmol) in toluene in a Schlenk flask. The reaction solution was slowly increased to room temperature and stirred at room temperature for 48 hours. After the reaction, the red suspension was filtered to obtain 4.43 g of red solid, which was benzyl potassium (BnK), with a yield of 68%.

[0158] The gas chromatography-mass spectrometry (GC-MS) analysis used in the following examples involved dissolving 1-2 mg of the reaction product obtained after the reaction in 1 mL of ethyl acetate, testing using the GCMS-Q2020 NX instrument to determine the molecular weight and abundance of the product, and then calculate deuteration rate using the IsoPat.sup.2 calculation method (the IsoPat.sup.2 calculation method of Reference J. Org. Chem. 2007, 72, 5778-5783. which is incorporated into this application by reference).

Example 1

Preparation of Deuterated 4-Phenyltoluene

[0159] ##STR00019##

[0160] Under an inert atmosphere, in a 25 mL autoclave, 4-phenyltoluene (CAS: 644-08-6) (0.0504 g, 0.3 mmol), deuterated benzene (0.5 mL), and potassium hydride (0.0012 g, 0.03 mmol, 10 mol %) were sequentially added. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 80 C. for 24 hours to undergo the deuteration reaction. After the reaction, the reaction solution was separated by column chromatography, and the obtained deuterated 4-phenyltoluene was subjected to nuclear magnetic resonance .sup.1HNMR and .sup.13C NMR testing, with .sup.1H NMR performed at a frequency of 400 MHz using deuterated chloroform as the deuterated solvent and .sup.13C NMR performed at a frequency of 101 MHz using deuterated chloroform as the deuterated solvent.

[0161] The deuteration rate was calculated based on .sup.1H NMR data, and the deuteration rate of the carbon-hydrogen bond at the benzyl position of deuterated 4-phenyltoluene was determined to be 31%.

Examples 2 to 20

[0162] Except for the preparation parameters and deuteration rates as shown in Table 2, the rest were the same as Example 1.

TABLE-US-00002 TABLE 2 Catalyst Column and its Deuterium chromatography molar Reaction Reaction gas Deuteration separation quantity temperature time pressure rate yield Example (mol %) ( C.) (h) (bar) Reaction solvent (%) (%) 1 KH (10) 80 24 4 C.sub.6D.sub.6 31 97 2 BnK (10) 80 24 4 C.sub.6D.sub.6 <10 98 3 KHMDS (10) 80 24 4 C.sub.6D.sub.6 30 97 4 NaHMDS (10) 80 24 4 C.sub.6D.sub.6 <5 97 5 LiHMDS (10) 80 24 4 C.sub.6D.sub.6 <5 97 6 CsF (10) + 80 24 4 C.sub.6D.sub.6 97 97 LiHMDS (10) 7 RbF (10) + 80 24 4 C.sub.6D.sub.6 90 98 LiHMDS (10) 8 Cs.sub.2CO.sub.3 (5) + 80 24 4 C.sub.6D.sub.6 75 98 LiHMDS (10) 9 CsF (10) 80 24 4 C.sub.6D.sub.6 <5 97 10 CsF (5) + 80 24 4 C.sub.6D.sub.6 87 97 LiHMDS (5) 11 CsF (10) + 80 36 4 C.sub.6D.sub.6 99 99 LiHMDS (10) 12 CsF (10) + 100 24 4 C.sub.6D.sub.6 98 99 LiHMDS (10) 13 CsHMDS (10) 80 24 4 C.sub.6D.sub.6 97 98 14 CsF (10) + 80 24 4 Benzene 96 96 LiHMDS (10) 15 CsF (10) + 80 24 4 Tetrahydrofuran 42 96 LiHMDS (10) 16 CsF (10) + 80 24 4 Ether 97 95 LiHMDS (10) 17 CsF (10) + 80 24 4 TBME 97 96 LiHMDS (10) 18 CsF (10) + 80 24 4 n-Hexane 95 95 LiHMDS (10) 19 CsF (10) + 80 24 4 Cyclohexane 96 96 LiHMDS (10) 20 CsF (30) + 80 24 1 Benzene 97 97 LiHMDS (30)

[0163] In Example 6, the .sup.1H NMR spectrum is shown in FIG. 1, .sup.1H NMR (400 MHz, CDCl.sub.3) 7.64-7.57 (m, 2H), 7.55-7.49 (m, 2H), 7.48-7.41 (m, 2H), 7.38-7.32 (m, 1H), 7.30-7.26 (m, 2H), 2.44-2.33 (in, 0.07H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 2, .sup.13C NMR (101 MHz, CDCl.sub.3) 141.3, 138.5, 137.1, 129.6, 128.9, 127.14, 127.12, 127.11, 20.8-20.2 (in, 1C, deuterated positions).

Example 21

Preparation of Deuterated p-Xylene

[0164] ##STR00020##

[0165] Under an inert atmosphere, in a 25 mL autoclave, p-xylene (CAS: 106-42-3) (0.0319 g, 0.3 mmol), deuterated benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were sequentially added. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 80 C. for 24 hours to undergo the deuteration reaction. Deuterium gas was then refilled to maintain a pressure of 4 bar for the deuterium gas inside the autoclave, and the reaction was continued for another 24 hours. After completion of the reaction, the reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR testing.

[0166] In Example 21, the .sup.1H NMR spectrum is shown in FIG. 3, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 6.98 (s, 4H), 2.17-2.05 (m, 0.39H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 4, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 134.7, 129.3, 20.6-19.8 (m, 2C, deuterated positions).

[0167] Based on the .sup.1H NMR data, the deuteration rate was calculated, and the deuteration rate of the carbon-hydrogen bond at the benzyl position on deuterated p-xylene was determined to be 94%.

Example 22

Preparation of Deuterated 4-Ethylbiphenyl

[0168] ##STR00021##

[0169] Under an inert atmosphere, in a 25 mL autoclave, 4-ethylbiphenyl (CAS: 5707-44-8) (0.0547 g, 0.3 mmol), benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0264 g, 0.09 mmol, 30 mol %) were added sequentially. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 80 C. for 24 hours to undergo the deuteration reaction. The reaction solution was then separated by column chromatography, with a separation yield of 98%. The obtained product was subjected to .sup.1H NMR and .sup.13C NMR testing using deuterated chloroform (CDCl.sub.3) as the deuterated solvent.

[0170] In Example 22, the .sup.1H NMR spectrum is shown in FIG. 5, .sup.1H NMR (400 MHz, CDCl.sub.3) 7.73-7.65 (m, 2H), 7.65-7.58 (m, 2H), 7.56-7.48 (m, 2H), 7.45-7.34 (m, 3H), 2.90-2.65 (m, 0.06H, deuterated positions), 1.43-1.30 (m, 3H). The .sup.13C NMR spectrum is shown in FIG. 6, .sup.13C NMR (101 MHz, CDCl.sub.3) 143.4, 141.3, 138.8, 128.8, 128.4, 127.2, 127.14, 127.09, 28.5-27.5 (m, 1C, deuterated positions), 15.6.

[0171] Based on the .sup.1H NMR data, the deuteration rate was calculated, and the deuteration rate of the carbon-hydrogen bond at the benzyl position on deuterated 4-ethylbiphenyl was determined to be 97%.

Example 23

Preparation of Deuterated 2-Methylpyridine

[0172] ##STR00022##

[0173] Under an inert atmosphere, in a 25 mL autoclave, 2-methylpyridine (CAS: 109-06-8) (0.0280 g, 0.3 mmol), deuterated benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR testing.

[0174] In Example 23, the .sup.1H NMR spectrum is shown in FIG. 7, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 8.61-8.32 (m, 1H), 7.07-6.98 (m, 1H), 6.71-6.57 (m, 2H), 2.47-2.30 (m, 0.23H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 8, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 158.8, 149.7, 135.6, 122.9, 120.6, 24.0-23.4 (m, 1C, deuterated positions).

[0175] Based on the .sup.1H NMR data, the deuteration rate was calculated, and the deuteration rate of the carbon-hydrogen bond at the benzyl position on deuterated 2-methylpyridine was determined to be 92%.

Example 24

Preparation of Deuterated 3-Methylpyridine

[0176] ##STR00023##

[0177] Under an inert atmosphere, in a 25 mL autoclave, 3-methylpyridine (CAS: 108-99-6) (0.0280 g, 0.3 mmol), deuterated benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR testing.

[0178] In Example 24, the .sup.1H NMR spectrum is shown in FIG. 9, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 8.44 (s, 2H), 6.90 (d, J=6.4 Hz, 1H), 6.79-6.60 (m, 1H), 1.87-1.69 (m, 0.55H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 10, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 150.9, 147.5, 135.8, 132.7, 123.0, 18.0-16.9 (m, 1C, deuterated positions).

[0179] Based on the .sup.1H NMR data, the deuteration rate was calculated, and the deuteration rate of the carbon-hydrogen bond at the benzyl position on deuterated 3-methylpyridine was determined to be 82%.

Example 25

Preparation of Deuterated 1,2-Dimethylindole

[0180] ##STR00024##

[0181] Under an inert atmosphere, in a 25 mL autoclave, 1,2-dimethylindole (CAS: 875-79-6) (0.0436 g, 0.3 mmol), benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0264 g, 0.09 mmol, 30 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was separated by column chromatography, with a separation yield of 97%. The obtained product was then subjected to .sup.1H NMR and .sup.13C NMR testing using deuterated chloroform (CDCl.sub.3) as the deuterated solvent.

[0182] In Example 25, the .sup.1H NMR spectrum is shown in FIG. 11, .sup.1H NMR (400 MHz, CDCl.sub.3) 7.65-7.54 (m, 1H), 7.35-7.27 (m, 1H), 7.25-7.19 (m, 1H), 7.18-7.10 (m, 1H), 6.24 (s, 1H), 3.69 (s, 3H), 2.58-2.34 (m, 0.31H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 12, .sup.13C NMR (101 MHz, CDCl.sub.3) 137.4, 136.8, 128.0, 120.5, 119.7, 119.3, 108.8, 99.5, 29.42, 12.8-11.9 (m, 1C, deuterated positions).

[0183] Based on the .sup.1H NMR data, the deuteration rate was calculated, and the deuteration rate of the carbon-hydrogen bond at the benzyl positions on deuterated 1,2-dimethylindole was determined to be 90%.

Example 26

Preparation of Deuterated 2-Methylbenzothiophene

[0184] ##STR00025##

[0185] Under an inert atmosphere, in a 25 mL autoclave, 2-methylbenzothiophene (CAS: 1195-14-8) (0.0445 g, 0.3 mmol), deuterated benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0264 g, 0.09 mmol, 30 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR testing.

[0186] In Example 26, the .sup.1H NMR spectrum is shown in FIG. 13, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 7.60-7.57 (m, 0.08H, deuterated positions), 7.56-7.49 (m, 1H), 7.25-7.15 (m, 1H), 7.13-7.04 (m, 1H), 6.67 (s, 0.03H, deuterated positions), 2.26-2.07 (m, 0.11H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 14, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 141.0, 140.6, 140.2, 124.4, 124.3, 123.8, 123.7, 122.9, 122.3-121.6 (m, 2C, deuterated positions), 15.2-14.4 (m, 1C, deuterated positions).

[0187] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rates of the carbon-hydrogen bonds at different deuterated positions on deuterated 2-methylbenzothiophene were obtained, as shown in the reaction Equation.

Example 27

Preparation of Deuterated Diphenylmethane

[0188] ##STR00026##

[0189] Under an inert atmosphere, in a 25 mL autoclave, diphenylmethane (CAS: 101-81-5) (0.0504 g, 0.3 mmol), benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was separated by column chromatography, with a separation yield of 94%. The resulting product was subjected to .sup.1H NMR and .sup.13C NMR testing using deuterated chloroform as the deuterated solvent.

[0190] In Example 27, the .sup.1H NMR spectrum is shown in FIG. 15, .sup.1H NMR (400 MHz, CDCl.sub.3) 7.43-7.34 (m, 4H), 7.34-7.24 (m, 6H), 4.14-3.99 (m, 0.06H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 16, .sup.13C NMR (101 MHz, CDCl.sub.3) 141.2, 129.1, 128.6, 126.2, 41.9-41.0 (m, 1C, deuterated positions).

[0191] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the benzyl position on deuterated diphenylmethane was found to be 97%.

Example 28

Preparation of Deuterated Benzyl Methyl Ether

[0192] ##STR00027##

[0193] Under an inert atmosphere, in a 25 mL autoclave, benzyl methyl ether (CAS: 538-86-3) (0.0366 g, 0.3 mmol), benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was separated by column chromatography, with a separation yield of 42%. The resulting product was subjected to .sup.1H NMR and .sup.13C NMR testing using deuterated chloroform as the deuterated solvent.

[0194] In Example 28, the .sup.1H NMR spectrum is shown in FIG. 17, .sup.1H NMR (400 MHz, CDCl.sub.3) 7.42-7.27 (m, 5H), 4.56-4.36 (m, 0.19H, deuterated positions), 3.39 (s, 3H). The .sup.13C NMR spectrum is shown in FIG. 18, .sup.13C NMR (101 MHz, CDCl.sub.3) 138.2, 128.5, 127.9, 127.8, 74.7-73.9 (m, labeled, 1C, deuterated positions), 58.2, 58.1.

[0195] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the benzyl position on deuterated benzyl methyl ether was found to be 91%.

Example 29

Preparation of Deuterated Benzyl Phenyl Sulfide

[0196] ##STR00028##

[0197] Under an inert atmosphere, in a 25 mL autoclave, benzyl phenyl sulfide (CAS: 831-91-4) (0.0601 g, 0.3 mmol), benzene (0.5 mL), and potassium bis(trimethylsilyl)amide (0.0060 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was separated by column chromatography, with a separation yield of 99%. The resulting product was subjected to .sup.1H NMR and .sup.13C NMR testing using deuterated chloroform as the deuterated solvent.

[0198] In Example 29, the .sup.1H NMR spectrum is shown in FIG. 19, .sup.1H NMR (400 MHz, CDCl.sub.3) 7.37-7.21 (m, 9H), 7.21-7.15 (m, 1H), 4.18-4.03 (m, 0.05H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 20, .sup.13C NMR (101 MHz, CDCl.sub.3) 137.4, 136.4, 130.8, 129.9, 128.9, 128.6, 127.2, 126.4, 38.8-38.1 (m, 1C, deuterated positions).

[0199] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the benzyl position on deuterated benzyl phenyl sulfide was found to be 98%.

Example 30

Preparation of Deuterated N-Ethyl-N-Benzyl Aniline

[0200] ##STR00029##

[0201] Under an inert atmosphere, in a 25 mL autoclave, N-ethyl-N-benzyl aniline (CAS: 92-59-1) (0.0634 g, 0.3 mmol), benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was subjected to column chromatography, with a separation yield of 98%. The resulting product was subjected to .sup.1H NMR and .sup.13C NMR testing using deuterated chloroform as the deuterated solvent.

[0202] In Example 30, the .sup.1H NMR spectrum is shown in FIG. 21, .sup.1H NMR (400 MHz, CDCl.sub.3) 7.49-7.21 (m, 7H), 6.90-6.71 (m, 3H), 4.75-4.47 (m, 0.35H, deuterated positions), 3.69-3.45 (m, 2H), 1.31 (t, J=7.0 Hz, 3H). The .sup.13C NMR spectrum is shown in FIG. 22, .sup.13C NMR (101 MHz, CDCl.sub.3) 148.6, 139.33, 139.27, 129.3, 128.6, 126.9, 126.7, 116.1, 112.2, 54.0-53.5 (m, 1C, deuterated positions), 45.2, 45.1, 12.2.

[0203] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the benzyl position on deuterated N-ethyl-N-benzyl aniline was found to be 83%.

Example 31

Preparation of Deuterated Phenyl Methyl Sulfide

[0204] ##STR00030##

[0205] Under an inert atmosphere, in a 25 mL autoclave, phenyl methyl sulfide (CAS: 100-68-5) (0.0372 g, 0.3 mmol), deuterated benzene (0.5 mL), and potassium bis(trimethylsilyl)amide (0.0060 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with deuterium gas to achieve the pressure of deuterium gas in the autoclave is 4 bar, heated at 60 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was subjected to .sup.1H NMR and .sup.13C NMR testing directly.

[0206] In Example 31, the .sup.1H NMR spectrum is shown in FIG. 23, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 7.13-7.08 (m, 2H), 7.04-6.99 (m, 2H), 6.93-6.87 (m, 1H), 1.97-1.93 (m, 0.19H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 24, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 139.2, 129.1, 126.9, 125.1, 15.4-14.5 (m, 1C, deuterated positions).

[0207] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the deuterated position in deuterated phenyl methyl sulfide was found to be 94%.

Example 32

Preparation of Deuterated Methylthiocyclohexyl Ester

[0208] ##STR00031##

[0209] Under an inert atmosphere, in a 25 mL autoclave, methylthiocyclohexyl ester (CAS: 7133-37-1) (0.0391 g, 0.3 mmol), deuterated benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 48 hours to undergo the deuteration reaction. Then, deuterium gas was refilled to maintain a pressure of 4 bar for the deuterium gas inside the autoclave, and the reaction was continued for another 48 hours. Afterward, the reaction solution was subjected to .sup.1H NMR and .sup.13C NMR testing, and the deuteration rate is shown in the figure.

[0210] In Example 32, the .sup.1H NMR spectrum is shown in FIG. 25, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 2.42-2.24 (m, 1H), 1.90-1.83 (m, 2H), 1.82-1.77 (m, 0.19H, deuterated positions), 1.64-1.57 (m, 2H), 1.45-1.40 (m, 1H), 1.31-1.23 (m, 2H), 1.12-1.05 (m, 3H). The .sup.13C NMR spectrum is shown in FIG. 26, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 45.0, 44.9, 33.5, 26.3, 26.2, 13.1-12.3 (m, 1C, deuterated positions).

[0211] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the deuterated position in deuterated methylthiocyclohexyl ester was found to be 93%.

Example 33

Preparation of Deuterated Dimethyl Sulfoxide

[0212] ##STR00032##

[0213] Under an inert atmosphere, in a 25 mL autoclave, dimethyl sulfoxide (CAS: 67-68-5) (0.0234 g, 0.3 mmol), deuterated benzene (0.5 mL), and potassium tert-butoxide (0.0034 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 48 hours to undergo the deuteration reaction. Subsequently, the reaction solution was treated with 1,3,5-Trimethoxybenzene (0.0218 g) as an internal standard, and then subjected to .sup.1H NMR and .sup.13C NMR testing. The .sup.1H NMR spectrum is shown in FIG. 27, and the .sup.13C NMR spectrum is shown in FIG. 28.

[0214] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rate of the the carbon-hydrogen bond at the deuterated position in deuterated dimethyl sulfoxide was found to be 91%.

Example 34

Preparation of Deuterated Phenyl Methyl Sulfoxide

[0215] ##STR00033##

[0216] Under an inert atmosphere, in a 25 mL autoclave, phenyl methyl sulfoxide (CAS: 1193-82-4) (0.0421 g, 0.3 mmol), deuterated benzene (0.5 mL), and potassium tert-butoxide (0.0034 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 48 hours to undergo the deuteration reaction. Subsequently, the reaction solution was subjected to .sup.1H NMR and .sup.13C NMR testing directly. The .sup.1H NMR spectrum is shown in FIG. 29, and the .sup.13C NMR spectrum is shown in FIG. 30.

[0217] The deuteration rates were calculated based on .sup.1H NMR data, to obtain the deuteration rates of the CH bonds at different deuterated positions in deuterated phenyl methyl sulfoxide, as shown in the reaction equation.

Example 35

Preparation of Deuterated N,N-dimethylmethanesulfonamide

[0218] ##STR00034##

[0219] Under an inert atmosphere, in a 25 mL autoclave, N,N-dimethylmethanesulfonamide (CAS: 918-05-8) (0.0370 g, 0.3 mmol), deuterated benzene (0.5 mL), and potassium tert-butoxide (0.0034 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 48 hours to undergo the deuteration reaction. Subsequently, the reaction solution was subjected to .sup.1H NMR and .sup.13C NMR testing directly. The .sup.1H NMR spectrum is shown in FIG. 31, and the .sup.13C NMR spectrum is shown in FIG. 32.

[0220] The deuteration rate was calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the deuterated position in deuterated N,N-dimethylmethanesulfonamide was found to be 72%.

Example 36

Preparation of Deuterated Anisole

[0221] ##STR00035##

[0222] Under an inert atmosphere, in a 25 mL autoclave, anisole (CAS: 100-66-3) (0.0324 g, 0.3 mmol), deuterated benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 24 hours to undergo the deuteration reaction. Deuterium gas was refilled to maintain a pressure of 4 bar for the deuterium gas inside the autoclave, and the reaction was continued for another 24 hours. Subsequently, the reaction solution was subjected to .sup.1H NMR and .sup.13C NMR analysis directly.

[0223] In Example 36, .sup.1H NMR hydrogen spectrum is shown in FIG. 33, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 7.15-7.09 (m, 2H), 6.88-6.78 (m, 1.07H, deuterated positions), 3.31 (s, 3H). The .sup.13C NMR carbon spectrum is shown in FIG. 34, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 160.2, 129.6, 120.8, 114.3-113.8 (m, 2C, deuterated positions), 54.6.

[0224] The deuteration rate was calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the deuterated position in deuterated anisole was found to be 97%.

Example 37

Preparation of Deuterated 1,3-Benzodioxole

[0225] ##STR00036##

[0226] Under an inert atmosphere, in a 25 mL autoclave, 1,3-benzodioxole (CAS: 274-09-9) (0.0367 g, 0.3 mmol), deuterated benzene (0.5 mL), and potassium bis(trimethylsilyl)amide (0.0180 g, 0.09 mmol, 30 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 24 hours to undergo the deuteration reaction. Subsequently, the reaction solution was subjected to .sup.1H NMR and .sup.13C NMR testing directly.

[0227] In Example 37, .sup.1H NMR hydrogen spectrum is shown in FIG. 35, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 6.71-6.64 (m, 0.20H, deuterated positions), 6.60 (s, 2H), 5.39-5.20 (m, 1.44H, deuterated positions). The .sup.13C NMR carbon spectrum is shown in FIG. 36, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 148.0, 121.8, 108.9-108.4 (m, 2C, deuterated positions), 100.6-100.0 (m, 1C, deuterated positions).

[0228] The deuteration rates were calculated based on .sup.1H NMR data to obtain the deuteration rates of the CH bonds at different deuterated positions in deuterated 1,3-benzodioxole, as shown in the reaction equation.

Example 38

Preparation of Deuterated 4-Fluorobiphenyl

[0229] ##STR00037##

[0230] Under an inert atmosphere, in a 25 mL autoclave, 4-fluorobiphenyl (CAS: 324-74-3) (0.0516 g, 0.3 mmol), benzene (0.5 mL), cesium fluoride (0.0046 g, 0.03 mmol, 10 mol %), and lithium bis(trimethylsilyl)amide (0.0050 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 24 hours to undergo the deuteration reaction. Subsequently, deuterium gas was refilled to maintain a pressure of 4 bar for the deuterium gas inside the autoclave, and the reaction was continued for another 24 hours. Then, the reaction solution was separated by column chromatography, with a separation yield of 98%. The obtained product was analyzed by .sup.1H NMR and .sup.13C NMR, using deuterated chloroform as the deuterated solvent.

[0231] In Example 38, .sup.1H NMR hydrogen spectrum is shown in FIG. 37, .sup.1H NMR (400 MHz, CDCl.sub.3) 7.59-7.50 (m, 4H), 7.48-7.40 (m, 2H), 7.38-7.31 (m, 1H), 7.18-7.08 (m, 0.05H, deuterated positions). The .sup.13C NMR carbon spectrum is shown in FIG. 38, .sup.13C NMR (101 MHz, CDCl.sub.3) 162.6 (d, J=246.4 Hz), 140.4, 137.4, 128.9, 128.7 (d, J=8.0 Hz), 127.4, 127.1, 115.8-115.1 (m, 2C, deuterated positions).

[0232] The deuteration rate was calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the deuterated position in deuterated 4-fluorobiphenyl was found to be 98%.

Example 39

Preparation of Deuterated 1,4-Difluorobenzene

[0233] ##STR00038##

[0234] Under an inert atmosphere, in a 25 mL autoclave, 1,4-difluorobenzene (CAS: 540-36-3) (0.0342 g, 0.3 mmol), deuterated benzene (0.5 mL), and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 24 hours to undergo the deuteration reaction. Subsequently, deuterium gas was refilled to maintain a pressure of 4 bar for the deuterium gas inside the autoclave, and the reaction was continued for another 24 hours. Then, dibromomethane (CAS: 74-95-3) (0.0264 g) was added to the reaction solution as an internal standard. The reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR testing.

[0235] In Example 39, .sup.1H NMR hydrogen spectrum is shown in FIG. 39, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 6.58-6.42 (m, 0.53H, deuterated positions), 3.97 (s, 2H, internal standard dibromomethane). the .sup.13C NMR carbon spectrum is shown in FIG. 40, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 159.0 (d, J=239.3 Hz), 116.6-115.8 (m, 4C, deuterated positions), 19.0 (Internal standard dibromomethane).

[0236] The deuteration rate was calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the deuterated position in deuterated 1,4-difluorobenzene was found to be 93%.

Example 40

Preparation of Deuterated Benzene

[0237] ##STR00039##

[0238] Under an inert atmosphere, in a 25 mL autoclave, benzene (CAS: 71-43-2) (0.5000 g, 6.4 mmol) and cesium bis(trimethylsilyl)amide (0.3000 g, 1.02 mmol, 16 mol %) were added sequentially. The autoclave was sealed, filled with 14 bar deuterium gas, heated at 120 C. for 60 hours to undergo the deuteration reaction. Subsequently, the reaction solution was separated and purified, added with mesitylene (2.1 mmol) as an internal standard, then subjected to .sup.1H NMR and .sup.13C NMR testing. .sup.1H NMR hydrogen spectrum is shown in FIG. 41, the .sup.13C NMR carbon spectrum is shown in FIG. 42.

[0239] The deuteration rate was calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the deuterated position in deuterated benzene was found to be 78%.

Example 41

Preparation of Deuterated Biphenyl

[0240] ##STR00040##

[0241] Under an inert atmosphere, in a 25 mL autoclave, biphenyl (CAS: 92-52-4) (0.0463 g, 0.3 mmol), benzene (0.5 mL) and cesium bis(trimethylsilyl)amide (0.0435 g, 0.15 mmol, 50 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 120 C. for 48 hours to undergo the deuteration reaction. Deuterium gas was refilled to maintain a pressure of 4 bar for the deuterium gas inside the autoclave, and the reaction was continued for another 48 hours. The average deuteration rate was determined to be 96% through the analysis using Gas Chromatography-Mass Spectrometry (GC-MS) and IsoPat.sup.2 software.

Example 42

Preparation of Deuterated Naphthalene

[0242] ##STR00041##

[0243] Under an inert atmosphere, in a 25 mL autoclave, naphthalene (CAS: 91-20-3) (0.0385 g, 0.3 mmol) benzene (0.5 mL) and cesium bis(trimethylsilyl)amide (0.0435 g, 0.15 mmol, 50 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 120 C. for 48 hours to undergo the deuteration reaction. The average deuteration rate was determined to be 81% through the analysis using Gas Chromatography-Mass Spectrometry (GC-MS) and IsoPat.sup.2 software.

Example 43

Preparation of Deuterated Triphenylamine

[0244] ##STR00042##

[0245] Under an inert atmosphere, in a 25 mL autoclave, triphenylamine (CAS: 603-34-9) (0.0736 g, 0.3 mmol), methyl tert-butyl ether (1.0 mL) and cesium bis(trimethylsilyl)amide (0.0435 g, 0.15 mmol, 50 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 120 C. for 48 hours to undergo the deuteration reaction. Deuterium gas was refilled to maintain a pressure of 4 bar for the deuterium gas inside the autoclave, and the reaction continued for another 48 hours. The average deuteration rate was determined to be 53% through the analysis using Gas Chromatography-Mass Spectrometry (GC-MS) and IsoPat.sup.2 software.

Example 44

Preparation of Deuterated N-Phenylcarbazole

[0246] ##STR00043##

[0247] Under an inert atmosphere, in a 25 mL autoclave, N-phenylcarbazole (CAS: 1150-62-5) (0.0730 g, 0.3 mmol), methyl tert-butyl ether (0.5 mL) and cesium bis(trimethylsilyl)amide (0.0435 g, 0.15 mmol, 50 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 100 C. for 24 hours to undergo the deuteration reaction. The average deuteration rate was determined to be 39% through the analysis using Gas Chromatography-Mass Spectrometry (GC-MS) and IsoPat.sup.2 software.

Example 45

Preparation of Deuterated Pyridine

[0248] ##STR00044##

[0249] Under an inert atmosphere, in a 25 mL autoclave, pyridine (CAS: 110-86-1) (0.0237 g, 0.3 mmol), deuterated benzene (0.5 mL) and cesium bis(trimethylsilyl)amide (0.0435 g, 0.15 mmol, 50 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 100 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was added with mesitylene (0.0120 g, 0.1 mmol) as an internal standard, and subjected to .sup.1H NMR and .sup.13C NMR testing. The .sup.1H NMR spectrum is shown in FIG. 43, and the .sup.13C NMR spectrum is shown in FIG. 44.

[0250] The deuteration rate was calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the deuterated position in deuterated pyridine was found to be 97%.

Example 46

Preparation of Deuterated 2-Phenylpyridine

[0251] ##STR00045##

[0252] Under an inert atmosphere, in a 25 mL autoclave, 2-phenylpyridine (CAS: 1008-89-5) (0.0467 g, 0.3 mmol), benzene (0.5 mL) and cesium bis(trimethylsilyl)amide (0.0435 g, 0.15 mmol, 50 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 100 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was separated and purified, added with mesitylene (0.0120 g, 0.1 mmol) as an internal standard, subjected to .sup.1H NMR and .sup.13C NMR testing. The .sup.1H NMR spectrum is shown in FIG. 45, and the .sup.13C NMR spectrum is shown in FIG. 46.

[0253] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rates of the carbon-hydrogen bonds at different positions in deuterated 2-phenylpyridine were obtained as shown in the reaction equation.

Example 47

Preparation of Deuterated 2,2-Bipyridine

[0254] ##STR00046##

[0255] Under an inert atmosphere, in a 25 mL autoclave, 2,2-bipyridine (CAS: 366-18-7) (0.0468 g, 0.3 mmol), ether (0.5 mL) and cesium bis(trimethylsilyl)amide (0.0435 g, 0.15 mmol, 50 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 100 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was separated and purified, and added with mesitylene (0.0120 g, 0.1 mmol) as an internal standard, subjected to .sup.1H NMR and .sup.13C NMR testing. The .sup.1H NMR spectrum is shown in FIG. 47.

[0256] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rates of the carbon-hydrogen bonds at different positions in deuterated 2,2-bipyridine were obtained as shown in the reaction equation.

Example 48

Preparation of Deuterated N-Methylindole

[0257] ##STR00047##

[0258] Under an inert atmosphere, in a 25 mL autoclave, N-methylindole (CAS: 603-76-9) (0.0394 g, 0.3 mmol), benzene (0.5 mL) and potassium bis(trimethylsilyl)amide (0.0060 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was separated by column chromatography with a separation yield of 95%. The obtained product was subjected to .sup.1H NMR and .sup.13C NMR testing, using deuterated chloroform (CDCl.sub.3) as the deuterated solvent.

[0259] In Example 47, .sup.1H NMR hydrogen spectrum is shown in FIG. 48, .sup.1H NMR (400 MHz, CDCl.sub.3) 7.74-7.66 (m, 1H), 7.42-7.35 (m, 1H), 7.33-7.25 (m, 1H), 7.21-7.14 (m, 1H), 7.13-7.07 (m, 0.04H, deuterated positions), 6.55 (s, 1H), 3.84 (s, 3H). The .sup.13C NMR carbon spectrum is shown in FIG. 49, .sup.13C NMR (101 MHz, CDCl.sub.3) 136.8, 128.6, 129.1-128.4 (m, 1C, deuterated positions), 121.6, 121.0, 119.4, 109.3, 101.8, 32.9.

[0260] The deuteration rate was calculated based on .sup.1H NMR data, the deuteration rate of the carbon-hydrogen bond at the deuterated position in deuterated N-methylindole was found to be 96%.

Example 49

Preparation of Deuterated Benzothiophene

[0261] ##STR00048##

[0262] Under an inert atmosphere, in a 25 mL autoclave, benzothiophene (CAS: 95-15-8) (0.0403 g, 0.3 mmol), deuterated benzene (0.5 mL) and potassium bis(trimethylsilyl)amide (0.0060 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR testing.

[0263] In Example 49, the .sup.1H NMR spectrum is shown in FIG. 50, .sup.1H NMR (400 MHz, C.sub.6D.sub.6) 7.64-7.48 (m, 2H), 7.18-7.09 (m, 1H), 7.05 (t, J=7.6 Hz, 1H), 6.99-6.93 (m, 0.67H, deuterated positions), 6.92-6.88 (m, 0.17H, deuterated positions). The .sup.13C NMR spectrum is shown in FIG. 51, .sup.13C NMR (101 MHz, C.sub.6D.sub.6) 140.2, 140.1, 126.4-126.2 (m, 1C, deuterated positions), 124.5, 124.4, 124.0 (1C, deuterated positions), 123.90, 123.86, 123.83, 122.7.

[0264] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rates of the carbon-hydrogen bonds at different positions in deuterated benzothiophene were obtained as shown in the reaction equation.

Example 50

Preparation of Deuterated -Methylstyrene

[0265] ##STR00049##

[0266] Under an inert atmosphere, in a 25 mL autoclave, $-methylstyrene (CAS: 637-50-3) (0.0355 g, 0.3 mmol), deuterated benzene (0.5 mL) and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR tests. The .sup.1H NMR spectrum is shown in FIG. 52.

[0267] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rates of the carbon-hydrogen bonds at different positions in deuterated P-methylstyrene were obtained as shown in the reaction equation.

Example 51

Preparation of Deuterated 2,3-Dihydrofuran

[0268] ##STR00050##

[0269] Under an inert atmosphere, in a 25 mL autoclave, 2,3-dihydrofuran (CAS: 1191-99-7) (0.0210 g, 0.3 mmol), deuterated benzene (0.5 mL) and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 120 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR testing. The .sup.1H NMR spectrum is shown in FIG. 53.

[0270] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rates of the carbon-hydrogen bonds at different positions in deuterated 2,3-dihydrofuran were obtained as shown in the reaction equation.

Example 52

Preparation of Deuterated 1,4-Dioxene

[0271] ##STR00051##

[0272] Under an inert atmosphere, in a 25 mL autoclave, 1,4-dioxene (CAS: 543-75-9) (0.0258 g, 0.3 mmol), deuterated benzene (0.5 mL) and cesium bis(trimethylsilyl)amide (0.0087 g, 0.03 mmol, 10 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 120 C. for 24 hours to undergo the deuteration reaction. Then, the reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR testing. The .sup.1H NMR spectrum is shown in FIG. 54.

[0273] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rates of the carbon-hydrogen bonds at different positions in deuterated 1,4-dioxene were obtained as shown in the reaction equation.

Example 53

Preparation of Deuterated 1,3-bis-(2,4,6-trimethylphenyl)imidazol-2-ylidene

[0274] ##STR00052##

[0275] Under an inert atmosphere, in a 25 mL autoclave, 1,3-bis-(2,4,6-trimethylphenyl)imidazol-2-ylidene (CAS: 141556-42-5) (0.0601 g, 0.2 mmol), deuterated benzene (0.5 mL) and potassium bis(trimethylsilyl)amide (0.0120 g, 0.06 mmol, 30 mol %) were added sequentially. The autoclave was sealed, filled with 4 bar deuterium gas, heated at 80 C. for 48 hours to undergo the deuteration reaction. Then, the reaction solution was directly subjected to .sup.1H NMR and .sup.13C NMR testing. The .sup.1H NMR spectrum is shown in FIG. 55.

[0276] The deuteration rates were calculated based on .sup.1H NMR data, the deuteration rates of the carbon-hydrogen bonds at different positions in deuterated 1,3-bis-(2,4,6-trimethylphenyl)imidazol-2-ylidene were obtained as shown in the reaction equation.

[0277] The above description represents preferred embodiments of the present application and are not intended to limit the scope of the present application. Any modifications, equivalent replacements, improvements, and the like made within the spirit and principles of the present application should be included within the scope of protection of the present application.