Transfer hydrogenation process and catalyst

Details Transfer hydrogenation process and catalyst Transfer hydrogenation process and catalyst

2007-07-31

2007-07-31

Davis, Brian (Department: 1621)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heavy metal containing

C502S152000, C502S166000, C502S167000, C546S139000, C546S144000, C546S148000, C546S150000, C548S469000, C548S490000, C556S137000, C556S138000, C564S085000, C564S248000, C564S269000, C564S271000, C564S272000, C564S273000, C564S274000, C564S275000, C564S278000, C564S279000, C564S463000, C568S061000, C568S715000, C568S814000

Reexamination Certificate

active

10433351

ABSTRACT:
A catalytic transfer hydrogenation process is provided. The catalyst employed in the process is a metal hydrocarbyl complex which is coordinated to defined bidentate ligands substituted with at least one group selected from an optionally substituted sulphonated hydrocarbyl group, a sulphonated perhalogenated hydrocarbyl group, or an optionally substituted sulphonated heterocyclyl group. Preferred metals include rhodium, ruthenium and iridium. Preferred bidentate ligands are diamines and aminoalcohols, particularly those comprising chiral centres. The hydrogen donor is advantageously a secondary alcohol or a mixture of triethylamine and formic acid. The process can be employed to transfer hydrogenate ketones and imines, which are preferably prochiral. Catalysts for use in such a process are also provided.

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Matsumura, Kazuhiko, et al, “Asymmetric Transfer Hydrogenation of α, β-Acetylenic Ketones”, J. Am. Chem Soc. vol. 119, No. 37, 1997, p. 8738-8739.
Bubert, Christian, et al, “Synthesis of water-soluble aminosulfonamide ligands and their application in enantioselective transfer hydrogenation”, Tetrahedron Letters, vol. 42, 2001, p. 4037-4039.
Thorpe, Tim, et al, “Efficient rhodium and iridium-catalysed asymmetric transfer hydrogenation using water-soluble amniosulfonamide ligands”, Tetrahedron Letters, vol. 42, 2001, p. 4041-4043.

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