Methods for the synthesis of polycyclic aromatic hydrocarbons and synthesis platforms for performing such syntheses are provided. Methods and platforms are provided that allow for the synthesis of aza-polycyclic aromatic hydrocarbons by an expedient ring assembly. Methods and platforms allow for a modular approach to synthesis that provide multiple new C—C bonds in sequential pericyclic reactions, thus giving access to compounds with multiple axes of substitution.

A method of preparing a 2,6 disubstituted anilines includes, reacting a 2-amino isophthalic acid diester with sufficient Grignard reagent R.sub.2CH.sub.2MgX to form the corresponding diol product, dehydrating the diol product to the corresponding dialkene; and hydrogenating the diol product to form the corresponding aniline. The 2,6 disubstituted anilines can be used to produce N-Heterocyclic Carbenes (NHCs). The NHCs can find application in various fields such as organic synthesis, catalysis and macromolecular chemistry. Palladium catalysts containing the NHCs are also described.

It is an object of the present invention to provide a catalyst for a cross-coupling reaction in which an organometallic complex is sufficiently immobilized on a carrier and an object product can be easily obtained. The catalyst for a cross-coupling reaction of the present invention has a carrier part composed of a synthetic resin and an organometallic complex part immobilized on the carrier part by chemical bonding, and has a structure represented by formula (P1), wherein in (P1) R.sup.1, R.sup.2 may be the same or different, and is a substituent such as a hydrogen atom. R.sup.3, R.sup.4, R.sup.5, R.sup.6, R.sup.8, R.sup.9 may be the same or different and are substituents, such as a hydrogen. X represents a halogen atom, and R.sup.7 represents a substituent having 3 to 20 carbon atoms with a π bond. RS1 represents the main chain of the synthetic resin precursors having —CH.sub.2OH group at their end.

##STR00001##

Process for the preparation of a compound of Formula (I): ##STR00001## the process comprising the reaction of a compound of Formula (II) with malononitrile in the presence of a base and a palladium catalyst, ##STR00002## wherein X, Y and Z, independently of each other, represent fluoro, chloro or C.sub.1-4alkyl; and L is a leaving group; with the proviso that 1 or 2 of X and Y are, independently of each other, fluoro or chloro.

Disclosed is a method for preparing a 1,3-dicarbonyl compound based on a metal hydride/palladium compound system. The method includes the following steps: suspending a palladium compound and a metal hydride in a solvent under the protection of nitrogen, then adding an electron-deficient olefin compound, reacting same at 0° C.-100° C. for 0.3 to 10 hours, then adding a saturated ammonium chloride aqueous solution to stop the reaction, and then subjecting same to extraction, evaporation until dryness, and column chromatography purification to obtain the 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used by the present invention are reagents easily obtained in a laboratory. Compared to a common hydrogen hydrogenation method, the method is easier to operate, and has a higher safety, mild conditions, and a high reaction yield.

The invention relates to a material in the form of a cellular solid monolith consisting of an inorganic oxide polymer. Said monolith comprises macropores which have an average size d.sub.A of 4 μm to 50 μm, mesopores that have an average size d.sub.E of 20 to 30 Å, and micropores which have an average size d.sub.1 of 5 à 10 Å, said pores being interconnected. The inorganic oxide polymer has organic groups R of formula —(CH.sub.2).sub.n—R.sup.1, wherein 0≤n≤5, and R.sup.1 is selected from among a thiol group, a pyrrole group, an amino group having one or more optional, optionally substituted alkyl, alkylamino, or aryl substituents, an alkyl group, or a phenyl group optionally having an alkyl-type substituent R.sup.2. The disclosed material can be used as a substrate for a metal catalyst and for decontaminating liquid or gaseous media.

2-(4-chloro-2,6-dimethyl-phenyl)propanedinitrile.

The invention relates to compounds of formula (I)

##STR00001##

where
R.sup.1, R.sup.2, R.sup.3, R.sup.4 are each independently selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl, —(C.sub.3-C.sub.20)-heteroaryl;
at least one of the R.sup.1, R.sup.2, R.sup.3, R.sup.4 radicals is a —(C.sub.3-C.sub.20)-heteroaryl radical;
and
R.sup.1, R.sup.2, R.sup.3, R.sup.4, if they are —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —(C.sub.6-C.sub.20)-aryl or —(C.sub.3-C.sub.20)-heteroaryl,
may each independently be substituted by one or more substituents selected from —(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.12)-cycloalkyl, —(C.sub.3-C.sub.12)-heterocycloalkyl, —O—(C.sub.1-C.sub.12)-alkyl, —O—(C.sub.1-C.sub.12)-alkyl-(C.sub.6-C.sub.20)-aryl, —O—(C.sub.3-C.sub.12)-cycloalkyl, —S—(C.sub.1-C.sub.12)-alkyl, —S—(C.sub.3-C.sub.12)-cycloalkyl, —COO—(C.sub.1-C.sub.12)-alkyl, —COO—(C.sub.3-C.sub.12)-cycloalkyl, —CONH—(C.sub.1-C.sub.12)-alkyl, —CONH—(C.sub.3-C.sub.12)-cycloalkyl, —CO—(C.sub.1-C.sub.12)-alkyl, —CO—(C.sub.3-C.sub.12)-cycloalkyl, —N—[(C.sub.1-C.sub.12)-alkyl].sub.2, —(C.sub.6-C.sub.20)-aryl, —(C.sub.6-C.sub.20)-aryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.6-C.sub.20)-aryl-O—(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl, —(C.sub.3-C.sub.20)-heteroaryl-(C.sub.1-C.sub.12)-alkyl, —(C.sub.3-C.sub.20)-heteroaryl-O—(C.sub.1-C.sub.12)-alkyl, —COOH, —OH, —SO.sub.3H, —NH.sub.2, halogen;
and to the use thereof as ligands in alkoxycarbonylation.

This invention relates to gels that undergo either oscillatory stepwise expansion or oscillatory expansion and contraction. An oscillatory reaction occurs within the gel, changing the conditions of the gel, and causing the gel to expand and optionally contract. The gels may be used for oscillatory release of a chemical agent.

An organometallic complex catalyst that makes it possible to obtain a higher yield of a desired product than conventional catalysts in a cross-coupling reaction. The organometallic complex catalyst has a structure represented by formula (1) and is for use in a cross-coupling reaction. In formula (1), M is the coordination center and represents a metal atom such as Pd or an ion thereof. R1, R2, and R3 may be the same or different and are a substituent such as a hydrogen atom. R4, R5, R6, and R7 may be the same or different and are a substituent such as a hydrogen atom. X represents a halogen atom. R8 represents a substituent that has a π bond and 3-20 carbon atoms. With regard to the electron-donating properties of R1-R7 with respect to the coordination center M of the ligand containing R1-R7 that is indicated in formula (2), R1-R7 are arranged in combination such that the TEP value obtained from infrared spectroscopy shifts toward the low frequency side compared to the TEP value of the ligand of formula (2-1). ##STR00001##