Enantioselective Copper-Catalyzed Defluoroalkylation Using Arylboronate-Activated Alkyl Grignard Reagents

A copper-catalyzed system has been introduced for the enantioselective defluoroalkylation of linear 1-(trifluoromethyl)­alkenes through C–F activation to synthesize various gem-difluoroalkenes as carbonyl mimics. For the first time, arylboronate-activated alkyl Grignard reagents were uncovered in th...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2018-07, Vol.140 (29), p.9061-9065
Main Authors: Wang, Minyan, Pu, Xinghui, Zhao, Yunfei, Wang, Panpan, Li, Zexian, Zhu, Chendan, Shi, Zhuangzhi
Format: Article
Language:English
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Summary:A copper-catalyzed system has been introduced for the enantioselective defluoroalkylation of linear 1-(trifluoromethyl)­alkenes through C–F activation to synthesize various gem-difluoroalkenes as carbonyl mimics. For the first time, arylboronate-activated alkyl Grignard reagents were uncovered in this cross-coupling reaction. Mechanistic studies confirmed that the tetraorganoborate complexes generated in situ were the key reactive species for this transformation.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.8b04902