Electrochemical Direct Formyloxylation of Benzylic C(sp3)–H with DMF

Herein, the first electrochemical strategy for direct acyloxylation of benzylic C­(sp3)–H with amides is described. The method features transition metal- and oxidant-free conditions with H2 evolution, the excellent functional group (including fluoro, chloro, bromo, iodo, cyano, trifluoromethyl, alde...

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Bibliographic Details
Published in:ACS sustainable chemistry & engineering 2023-02, Vol.11 (5), p.1624-1630
Main Authors: Wang, Xiao-Wen, Deng, Yang, Li, Rui-Xue, Lv, Jin-Feng, Fu, Ming-Qiu-Hao, Guan, Zhi, Zhao, Ya-Nan, He, Yan-Hong
Format: Article
Language:English
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Summary:Herein, the first electrochemical strategy for direct acyloxylation of benzylic C­(sp3)–H with amides is described. The method features transition metal- and oxidant-free conditions with H2 evolution, the excellent functional group (including fluoro, chloro, bromo, iodo, cyano, trifluoromethyl, aldehyde, ketone, carboxyl, ester, and ether) tolerance, up to 82% yield in an operation-friendly undivided cell under the open air, and ease of scale up. A number of well-designed mechanistic experiments [e.g., radical trapping, electron paramagnetic resonance (EPR) and isotope labeling] strongly support the radical-involved process of benzylic C­(sp3)–H functionalization and the process of amide C–N bond breaking.
ISSN:2168-0485
2168-0485
DOI:10.1021/acssuschemeng.2c05785