Disclosed is a zinc-imidazole complex mixed catalyst. Also disclosed are a method for preparing the zinc-imidazole complex mixed catalyst and a method for producing a methyl N-phenyl carbamate in high yield with high selectivity in the presence of the catalyst. The zinc-imidazole complex mixed catalyst can be reused due to its high reaction stability. In addition, the use of the zinc-imidazole complex mixed catalyst leads to a marked improvement in the production yield of a methyl N-phenyl carbamate with high selectivity.

An organometallic complex catalyst is disclosed 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. R.sup.1, R.sup.2, and R.sup.3 may be the same or different and are a substituent such as a hydrogen atom. R.sup.4, R.sup.5, R.sup.6, and R.sup.7 may be the same or different and are a substituent such as a hydrogen atom. X represents a halogen atom. R.sup.8 represents a substituent that has a bond and 3-20 carbon atoms. With regard to the electron-donating properties of R.sup.1-R.sup.7 with respect to the coordination center M of the ligand containing R.sup.1-R.sup.7 that is indicated in formula (2), R.sup.1-R.sup.7 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##

The invention relates to ylide-functionalized phosphane ligands, the production of same and use in transition metal compounds, as well as the use of same as catalysts in organic reactions.

The disclosure relates to a dual catalytic method for forming aryl carbon-nitrogen bonds. The method comprises contacting an aryl halide with an amine in the presence of a dual catalytic solution comprising a Ni(II) salt catalyst, a photocatalyst, and an optional base, thereby forming a reaction mixture; exposing the reaction mixture to light under reaction condition sufficient to produce the aryl carbon-nitrogen bonds. In certain embodiments, the amine may be present in a molar excess to the aryl halide. In certain embodiment, the photocatalyst may be [Ru(bpy).sub.3]Cl.sub.2 or an organic phenoxazine. In certain embodiments, the Ni salt catalyst solution includes a Ni(II) salt and a polar solvent, wherein the Ni(II) salt is dissolved in the polar solvent.

Reactions that directly install nitrogen into CH bonds of complex molecules are significant because of their potential to change the chemical and biological properties of a given compound. Selective intramolecular CH amination reactions that achieve high levels of reactivity, while maintaining excellent site-selectivity and functional-group tolerance is a challenging problem. Herein is reported a manganese perchlorophthalocyanine catalyst [Mn.sup.III(ClPc)] for intermolecular benzylic CH amination of bioactive molecules and natural products that proceeds with unprecedented levels of reactivity and site-selectivity. In the presence of Brnsted or Lewis acid, the [Mn.sup.III(ClPc)]-catalyzed CH amination demonstrates unique tolerance for tertiary amine, pyridine and benzimidazole functionalities. Mechanistic studies indicate that CH amination proceeds through an electrophilic metallonitrene intermediate via a stepwise pathway where CH cleavage is the rate-determining step of the reaction. Collectively these mechanistic features contrast previous base-metal catalyzed CH aminations. The catalyst can be a compound of Formula I: ##STR00001##

The present invention provides a novel cationic ruthenium complex which is easy to produce and handle and can be procured at a relatively low cost and a production method for the ruthenium complex, a method for producing an alcohol or the like using the ruthenium complex as a catalyst, a method for producing a carbonyl compound using the ruthenium complex as a catalyst, and a method for producing a N-alkylamine compound using the ruthenium complex as a catalyst. The present invention pertains to a ruthenium complex represented by general formula (1): [RuX(CO).sub.2(PNP)]Y (wherein, X represents a monovalent anionic monodentate ligand, Y represents a counter anion, PNP represents a tridentate ligand, and CO represents carbon monoxide), a production method for the ruthenium complex, a catalyst containing the ruthenium complex, and a production method for various organic compounds using the catalyst.

The present invention provides a complex of formula (1), ##STR00001##
wherein, M is palladium or nickel, R.sub.1 and R.sub.2 are independently organic groups having 1-20 carbon atoms, or R.sub.1 and R.sub.2 are linked to form a ring structure with the phosphorus atom, R.sub.3 is selected from the group consisting of substituted and unsubstituted aryl, substituted and unsubstituted heteroaryl, and substituted and unsubstituted metallocenyl, R.sub.4 is an organic group having 1-20 carbon atoms, n is 0, 1, 2, 3, 4 or 5, and X is an anionic ligand. The invention also provides a process for the preparation of the complex, and its use in carbon-carbon or carbon-nitrogen coupling reactions.

Disclosed is a zinc-imidazole complex mixed catalyst. Also disclosed are a method for preparing the zinc-imidazole complex mixed catalyst and a method for producing a methyl N-phenyl carbamate in high yield with high selectivity in the presence of the catalyst. The zinc-imidazole complex mixed catalyst can be reused due to its high reaction stability. In addition, the use of the zinc-imidazole complex mixed catalyst leads to a marked improvement in the production yield of a methyl N-phenyl carbamate with high selectivity.

The present invention provides a palladium precatalyst for cross-coupling reaction, the palladium precatalyst comprising a structure represented by following formula 1: ##STR00001## wherein, R.sub.1 and R.sub.2 are the same, and R.sub.1 and R.sub.2 are substituted or unsubstituted phenyl; R.sub.3 and R.sub.4 are the same, and R.sub.3 and R.sub.4 are substituted or unsubstituted phenyl or cyclohexyl.

Disclosed are compounds, methods, reagents, systems, and kits for the preparation and utilization of monomeric or polymeric metal-based compounds. These metal-based compounds are organometallic catalysts composed of substituted dipyrrin ligands bound to transition metals. CH bond functionalization catalysis can be performed with the disclosed organometallic catalysts to yield CN bonds to generate substituted bicyclic, spiro, and fused nitrogen-containing heterocycles, all common motifs in various pharmaceutical and bioactive molecules.