American Chemical Society
Browse
jo7b02676_si_001.pdf (2.76 MB)

Switchable Chemoselective Transfer Hydrogenations of Unsaturated Carbonyls Using Copper(I) N‑Donor Thiolate Clusters

Download (2.76 MB)
journal contribution
posted on 2018-01-09, 00:00 authored by Meng-Juan Zhang, Da-Wei Tan, Hong-Xi Li, David James Young, Hui-Fang Wang, Hai-Yan Li, Jian-Ping Lang
Unsaturated alcohols and saturated carbonyls are important chemical, pharmaceutical, and biochemical intermediates. We herein report an efficient transfer hydrogenation protocol in which conversion of unsaturated carbonyl compounds to either unsaturated alcohols or saturated carbonyls was catalyzed by Cu­(I) N-donor thiolate clusters along with changing hydrogen source (isopropanol or butanol) and base (NaOH or K2CO3). Mechanistic studies supported by DFT transition state modeling indicate that such a chemoselectivity can be explained by the relative concentrations of Cu­(I) monohydride and protonated Cu­(I) hydride complexes in each catalytic system.

History