Electrosynthesis of 2‑Substituted Benzoxazoles via Intramolecular Shono-Type Oxidative Coupling of Glycine Derivatives

Herein, an atom-economical and eco-friendly electrochemical oxidation/cyclization of glycine derivatives through intramolecular Shono-type oxidative coupling is disclosed, leading to a variety of 2-substituted benzoxazoles in 51–85% yields. This oxidative cyclization proceeded in transition metal- a...

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Veröffentlicht in:Journal of organic chemistry 2022-09, Vol.87 (17), p.11379-11386
Hauptverfasser: Liu, Lei, Xu, Zhenhui, Liu, Tao, Xu, Chao, Zhang, Wangqin, Hua, Xiangqi, Ling, Fei, Zhong, Weihui
Format: Artikel
Sprache:eng
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Zusammenfassung:Herein, an atom-economical and eco-friendly electrochemical oxidation/cyclization of glycine derivatives through intramolecular Shono-type oxidative coupling is disclosed, leading to a variety of 2-substituted benzoxazoles in 51–85% yields. This oxidative cyclization proceeded in transition metal- and oxidant-free conditions and generated H2 as only a byproduct. Additionally, gram-scale reactions and a broad substrate scope demonstrated the synthetic usefulness of this protocol.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c00856