Hydride-mediated homogeneous catalysis. Catalytic reduction of. alpha. ,. beta. -unsaturated ketones using ((Ph sub 3 P)CuH) sub 6 and H sub 2

Journal Article · Wed Nov 22 04:00:00 EST 1989 · Journal of the American Chemical Society; (USA)

DOI:https://doi.org/10.1021/ja00206a008· OSTI ID:7157203

Mahoney, W S; Stryker, J M ^[1]

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1. Indiana Univ., Bloomington (USA)

Hydride-mediated reduction of {alpha},{beta}-unsaturated ketones catalytic in the hydride reagent is reported using ((Ph{sub 3}P)CuH){sub 6} and molecular hydrogen. The reaction proceeds at room temperature and is highly regioselective, affording either the product of conjugate reduction or complete 1,4- and 1,2-reduction to the saturated alcohol, depending on reaction conditions. In the presence of excess phosphine, the process is homogeneous and chemoselective: isolated double bonds are not hydrogenated, even under forcing conditions. This novel catalytic reduction appears to proceed via the heterolytic activation of molecular hydrogen by highly reactive copper(I) enolate and alkoxide intermediates.

• OSTI ID: 7157203
• Journal Information: Journal of the American Chemical Society; (USA), Journal Name: Journal of the American Chemical Society; (USA) Vol. 111:24; ISSN 0002-7863; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

08 HYDROGEN
080800 -- Hydrogen-- Properties & Composition
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400000* -- Chemistry
400201 -- Chemical & Physicochemical Properties
CATALYSIS
CHEMICAL REACTIONS
DATA
DATA ANALYSIS
ELEMENTS
EXPERIMENTAL DATA
HYDROGEN
HYDROGENATION
INFORMATION
KETONES
MEASURING INSTRUMENTS
MEASURING METHODS
NONMETALS
NUMERICAL DATA
ORGANIC COMPOUNDS
REDUCTION