An analytical device configured for the introduction of the liquid or solid sample into a sample chamber where it is extracted by a chlorinated hydrocarbon solvent, wherein the extract then passes into a chamber where it undergoes a Friedel-Crafts (FC) reaction.

The invention provides compounds of general structure I: (Ar.sup.1—Ar.sup.2—Ar.sup.3-E-P(=D)R.sub.2-).sub.nM.sub.mX.sub.nL.sub.n″. In this structure: •Ar.sup.1, Ar.sup.2 and Ar.sup.3 are aromatic groups wherein: —Ar.sup.1 and Ar.sup.3 are in a 1,3 relationship on Ar.sup.2, —each of Ar.sup.1, Ar.sup.2 and Ar.sup.3 optionally comprises one or more ring substituents of formula YR′.sub.r wherein each Y independently is absent or is O, S, B, N or Si and each R′ is independently H, halogen, alkyl, cycloalkyl, aryl or heteroaryl and r is 1, 2 or 3, where r is 1 if Y is absent or is O or S, 2 if Y is B or N and 3 if Y is Si, —Ar.sup.1, Ar.sup.2 and Ar.sup.3 are each independently carbocyclic or heterocyclic and each is independently monocyclic, bicyclic or polycyclic and each ring of each of Ar.sup.1, Ar.sup.2 and Ar.sup.3 independently has 5, 6 or 7 ring atoms; •E is absent or is selected from the group consisting of O, S, NR″, SiR″.sub.2, AsR″.sub.2 and CR″.sub.2; •M is a complexing metal; •X is selected from the group consisting of H, F, Br, CI, I, OTf, dba (dibenzylidene acetone), OC(═O)CF.sub.3 and OAc; •L is selected from the group consisting of PR″.sub.2, NR″.sub.2, OR″, SR″, SiR″.sub.3, AsR″.sub.3, alkene, alkyne, aryl and heteroaryl, each of said alkene, alkyne, aryl and heteroaryl being optionally substituted, for example with one or more halogens and/or with one or more R groups as defined herein; •each R is independently alkyl, cycloalkyl, heterocyclyl, heterocycloalkyl, aryl or -, heteroaryl; •D is absent or is ═S or —O or —Z-linker-Z—, where each Z independently is O or NH or N-alkyl and linker is an alkyl chain of 2-5 carbon atoms in length; •each R″ is independently H, alkyl, cycloalkyl, heterocycloalkyl, aryl or heteroaryl, each other than H being optionally substituted, or R″.sub.2 is —Z-linker-Z— as defined above; and •m is 0 or 1 or 2; wherein if m is 0, n is 1, n′ and n″ are 0 and -- is absent; and if m is 1 or 2, n is 1 or 2 and n′ and n″ are integers such that the coordination sphere of M is filled, and D is absent.

The present application describes process for preparing an ortho-allylated hydroxy aryl compounds such as compounds of Formula (I) by reacting an allylic alcohol with a hydroxy aryl compound in the presence of aluminum compound selected from alumina and aluminum alkoxides and in a non-protic solvent wherein at least one carbon atom ortho to the hydroxy group in the hydroxy aryl compound is unsubstituted. The present application also includes compounds of Formula (I).

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The present disclosure provides methods for conducting chemical reactions and for conducting a multi-step chemical reactions using swellable organically modified silica (SOMS) as nanoreactors.

In one aspect, phosphine compounds comprising three adamantyl moieties (PAd.sub.3) and associated synthetic routes are described herein. Each adamantyl moiety may be the same or different. For example, each adamantyl moiety (Ad) attached to the phosphorus atom can be independently selected from the group consisting of adamantane, diamantane, triamantane and derivatives thereof. Transition metal complexes comprising PAd.sub.3 ligands are also provided for catalytic synthesis including catalytic cross-coupling reactions.

Provided are new nickel./zirconium-mediated coupling reactions useful in the synthesis of ketone-containing compounds, e.g., halichondrin natural products and related molecules. A feature of the present disclosure is the use of a nickel(I) catalyst in tandem with a nickel (II) catalyst in the Ni/Zr-mediated coupling reactions. Without wishing to be bound by any particular theory, the nickel (I) catalyst selectively activates the electrophilic coupling partner (i.e., the compound of Formula (A)), and the nickel(ll) catalyst selectively activates the nucleophilic coupling partner (i.e., a thioester of Formula (B)). This dual catalyst system leads to improved coupling efficiency and eliminates the need for a large excess of one of the coupling partners (i.e., a compound of Formula (A) or (B)).

The invention discloses a mixed Ni(II) complex containing bisoxazoline-derived nitrogen heterocyclic carbene ligand and phosphite ligand and application thereof; the chemical formula of the mixed Ni(II) complex is Ni(NHC)[P(OR).sub.3]X.sub.2, wherein R is ethyl or isopropyl, X is bromine or chlorine, and NHC is a bisoxazoline-derived nitrogen heterocyclic carbene ligand. In the presence of magnesium shavings, the mixed Ni(II) complex containing bisoxazoline-derived nitrogen heterocyclic carbene ligand and phosphite ligand of the present invention can catalyze low-activity chlorinated aromatic hydrocarbons and fluorinated aromatic hydrocarbons with chlorinated benzyl compounds, respectively, reductive cross-coupling reaction at a single temperature, generating a diarylmethane compound in one step, providing a new method for the synthesis of diarylmethane compounds.

The invention discloses a tetramethyl-7,7′-spirobiindane-based phosphinooxazoline ligand compound and its preparation method and use. The phosphinooxazoline ligand compound is a compound having a structure shown in general formula I or an enantiomer, a raceme or a diastereoisomer thereof. The phosphinooxazoline ligand obtained through a series of reaction steps using cheap and easily available 3,3,3′,3′-tetramethyl-1,1′-spirobiindane-6,6′-diol as a starting material. The novel phosphinooxazoline ligand developed in the invention can be used to organic catalytic reactions, especially as a chiral phosphinooxazoline ligand widely used in metal-asymmetric catalytic reactions, having economical practicality and industrial application prospects. ##STR00001##

A method includes: providing a mixture including at least one alkyl tosylate and a Grignard reagent; and reacting the at least one alkyl tosylate with the Grignard reagent in a C—C coupling reaction mechanism to form a branched aliphatic alcohol.

Multiple methods of synthesizing cannabigerol are presented. Combining olivetol with geraniol derivatives are provided. Cross-coupling methods of combing functionalized resorcinols are provided. Useful intermediates are formed during such cross-coupling steps.