Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 15, Pages 6167-6172Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.9b02338
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Funding
- National Science Foundation of China [21822103, 21820102003, 21822303, 21772052, 21772053, 21572074, 21472057]
- Program of Introducing Talents of Discipline to Universities of China (111 Program) [B17019]
- Natural Science Foundation of Hubei Province [2017AHB047]
- International Joint Research Center for Intelligent Biosensing Technology and Health
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The first asymmetric propargylic radical cyanation was realized through a dual photoredox and copper catalysis. An organic photocatalyst serves to both generate propargyl radicals and oxidize Cu(I) species to Cu(II) species. A chiral Cu complex functions as an efficient organometallic catalyst to resemble the propargyl radical and cyanide in an enantio-controlled manner. Thus, a diverse range of optically active propargyl cyanides were produced with high reaction efficiency and enantioselectivities (28 examples, 57-97% yields and 83-98% ee). Moreover, mechanistic investigations including experiments and density functional theory calculations were performed to illustrate on the reaction pathway and stereochemical results.
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