1. Enantioselective reductive cross-couplings to forge C(sp2)–C(sp3) bonds by merging electrochemistry with nickel catalysis.
- Author
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Wang, Yun-Zhao, Sun, Bing, Guo, Jian-Feng, Zhu, Xiao-Yu, Gu, Yu-Cheng, Han, Ya-Ping, Ma, Cong, and Mei, Tian-Sheng
- 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. Reductive cross-coupling of aryl chlorides or electron-rich aryl bromides with benzyl chlorides remains a significant challenge, presumably due to the lower reactivity of aryl chlorides or electron-rich aryl bromides with the nickel catalyst compared with aryl iodides. Here, the authors present Ni-catalyzed enantioselective electroreductive cross-coupling of benzyl chlorides with aryl halides, yielding chiral 1,1-diaryl compounds with good to excellent enantioselectivity, without resorting to heterogeneous metal reductants or sacrificial anodes. [ABSTRACT FROM AUTHOR] more...- Published
- 2025
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