Enantioselective reductive cross-couplings to forge C(sp(2))-C(sp(3)) bonds by merging electrochemistry with nickel catalysis

通过将电化学与镍催化相结合,实现对映选择性还原交叉偶联以构建C(sp(2))-C(sp(3))键

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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 Ni(I) species activate aryl halides via oxidative addition and alkyl chlorides via single electron transfer.

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