para-Selective, Direct C(sp2)–H Alkylation of Electron-Deficient Arenes by the Electroreduction Process

Direct para-selective C­(sp2)–H alkylation of electron-deficient arenes based on the electroreduction-enabled radical addition of alkyl bromides has been developed under mild conditions. In the absence of any metals and redox agents, the simple electrolysis system tolerates a variety of primary, sec...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-05, Vol.88 (9), p.5248-5253
Main Authors: Ni, Pufan, Yang, Lei, Yang, Jiasheng, Cheng, Ruihua, Zhu, Weiping, Ma, Yueyue, Ye, Jinxing
Format: Article
Language:English
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Summary:Direct para-selective C­(sp2)–H alkylation of electron-deficient arenes based on the electroreduction-enabled radical addition of alkyl bromides has been developed under mild conditions. In the absence of any metals and redox agents, the simple electrolysis system tolerates a variety of primary, secondary, and tertiary alkyl bromides and behaves as an important complement to the directed alkylation of the C­(sp2)–H bond and the classic Friedel-Crafts alkylation. This electroreduction process provides a more straightforward, environmentally benign, and effective alkylation method for electron-deficient arenes.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c02412