Method for producing coupling compound

Catalyst – solid sorbent – or support therefor: product or process – Catalyst or precursor therefor – Organic compound containing

Reexamination Certificate

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C548S312400

Reexamination Certificate

active

10757148

ABSTRACT:
A method is provided for producing a specific crosscoupling compound and a specific catalyst for producing the compound. The method includes reacting in the presence of a base and a nickel compound catalyst organic halide of the formula n′(R1X1n), wherein R1is a hydrocarbon group and the α and β carbons to X′ are sp3carbon atoms; X1is a chlorine, bromine, or iodine atoms, and n and n1and 1 or 2 but not both 2, with a compound having the formula m{R2(BX22)n′} where an R2is an aryl, heteroaryl, or alkenyl group, and n′ is 1 or 2, X2is independently a hydroxyl group, an alkoxy or arylalkoxy group or X22together form an alkylenedioxy or arylenedioxy group, and m represents 1 or 2 but m≦n, and the boron atom is bonded to a sp2carbon atom of R2group or a boronic acid trimer anhydride.

REFERENCES:
patent: WO 01/66248 (2001-09-01), None
Katalin OSZa, “Copper(II), nickel(II) and zinc(II) complexes of amino acids containing bis(imidazol-2-yl)methyl residues”,Inorganica Chimica Acta, vol. 339, pp. 373-382, (2002).
Netherton et al., “Suzuki Cross-Coupling of Alkyl Tosylates that Possess β Hydrogen Atoms: Synthetic and Mechanistic Studies”,Angew. Chem. Int. Ed., vol. 41 No. 20, pp. 3910-3912, (2002).
Leadbeater et al., “Suzuki Aryl Couplings Mediated By Phosphine-Free Nickel Complexes”,Tetrahedron, vol. 55, pp. 11889-11894, (1999).
Elgafi et al., “Synthesis of novel ruthenium complexes containing bidentate imidazole-based ligands”,J. Chem Soc. Dalton Trans., pp. 2341-2345, (1997).
Satake, “Synthesis of Neutral π-Allypalladium Complexes having Bisnitrogen Ligands and Palladium-Catalyzed Cyclopropanation of Ketene Silyl Acetals with Allylic Acetates”,Journal of Synthetic Organic Chemistry, vol. 58, No. 8, pp. 736-744, (2000).

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