期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 135, 期 27, 页码 10022-10025出版社
AMER CHEMICAL SOC
DOI: 10.1021/ja404342j
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资金
- Princeton University
- ACS-PRF
Concerted proton-coupled electron transfer is a key mechanism of substrate activation in biological redox catalysis. However, its applications in organic synthesis remain largely unexplored. Herein, we report the development of a new catalytic protocol for ketyl-olefin coupling and present evidence to support concerted proton-coupled electron transfer being the operative mechanism of ketyl formation. Notably, reaction outcomes were correctly predicted by a simple thermodynamic formalism relating the oxidation potentials and pK(a) values of specific Bronsted acid/reductant combinations to their capacity to act jointly as a formal hydrogen atom donor.
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