American Chemical Society
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Enantioselective Copper-Catalyzed Defluoroalkylation Using Arylboronate-Activated Alkyl Grignard Reagents

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journal contribution
posted on 2018-07-10, 18:20 authored by Minyan Wang, Xinghui Pu, Yunfei Zhao, Panpan Wang, Zexian Li, Chendan Zhu, Zhuangzhi Shi
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.