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

M J Zhang; D W Tan; H X Li; David James Young; H F Wang; H Y Li; J P Lang

doi:10.1021/acs.joc.7b02676

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

Journal article

Peer reviewed

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

M J Zhang, D W Tan, H X Li, David James Young, H F Wang, H Y Li and J P Lang

Journal of Organic Chemistry, Vol.83(3), pp.1204-1215

2018

DOI: https://doi.org/10.1021/acs.joc.7b02676

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Abstract

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. © 2018 American Chemical Society.

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Title: Switchable Chemoselective Transfer Hydrogenations of Unsaturated Carbonyls Using Copper(I) N-Donor Thiolate Clusters
Authors: M J Zhang (Author) - Soochow University, People's Republic of China
D W Tan (Author) - Soochow University, People's Republic of China
H X Li (Author) - Soochow University, People's Republic of China
David James Young (Author) - University of the Sunshine Coast - Faculty of Science, Health, Education and Engineering
H F Wang (Author) - Soochow University, People's Republic of China
H Y Li (Author) - Soochow University, People's Republic of China
J P Lang (Author) - Soochow University, People's Republic of China
Publication details: Journal of Organic Chemistry, Vol.83(3), pp.1204-1215
Publisher: American Chemical Society
Date published: 2018
DOI: 10.1021/acs.joc.7b02676
ISSN: 0022-3263
Organisation Unit: University of the Sunshine Coast, Queensland
Language: English
Record Identifier: 99450728402621
Output Type: Journal article

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Collaboration types: Domestic collaboration; International collaboration
Web Of Science research areas: Chemistry, Organic