Highly Chemoselective Catalytic Hydrogenation of Unsaturated Ketones and Aldehydes to Unsaturated Alcohols Using Phosphine-Stabilized Copper(I) Hydride Complexes

✍ Scribed by Jian-Xin Chen; John F. Daeuble; Donna M. Brestensky; Jeffrey M. Stryker

• Book ID: 104209844
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 310 KB
• Volume: 56
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)01098-4

✦ Synopsis

AbstractÐA base metal hydrogenation catalyst composed of the phenyldimethylphosphine-stabilized copper(I) hydride complex provides for the highly chemoselective hydrogenation of unsaturated ketones and aldehydes to unsaturated alcohols, including the regioselective 1,2-reduction of a,b-unsaturated ketones and aldehydes to allylic alcohols. The active catalyst can be derived in situ by phosphine exchange using commercial [(Ph 3 P)CuH] 6 or from the reaction of copper(I) chloride, sodium tert-butoxide, and dimethylphenylphosphine under hydrogen. The catalyst derived from 1,1,1-tris(diphenylphosphinomethyl)ethane is mechanistically interesting but less synthetically useful.