Enantioselective reductive cross-couplings to forge C(sp2)-C(sp3) bonds by merging electrochemistry with nickel
Yun-Zhao Wang1, Bing Sun1, Jian-Feng Guo1
1State Key Laboratory of Organometallic Chemistry, Shanghai of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, PR China.
Abstract:
Motivated by the inherent benefits of synergistically combining electrochemical methodologies with nickel catalysis, we present here a Ni-catalyzed enantioselective electroreductive cross-coupling of benzyl chlorides with aryl halides, yielding chiral 1,1-diaryl compounds with good to excellent enantioselectivity. This catalytic reaction can not only be applied to aryl chlorides/bromides, which are challenging to access by other means, but also to benzyl chlorides containing silicon groups. Additionally, the absence of a sacrificial anode lays a foundation for scalability. The combination of cyclic voltammetry analysis with electrode potential studies suggests that NiI species activate aryl halides via oxidative addition and alkyl chlorides via single electron transfer.
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