The involvement of the trisulfur radical anion in electron-catalyzed sulfur insertion reactions: facile synthesis of benzothiazine derivatives under transition metal-free conditions

Chemical Science
Zheng-Yang GuShun-Jun Ji

Abstract

An efficient and practical synthesis of benzothiazine by K2S initiated sulfur insertion reaction with enaminones via electron catalysis is developed. This protocol provides a new, environment-friendly and simple strategy to construct benzothiazine derivatives via formation of two C-S bonds under transition metal-free, additive-free and oxidant-free conditions. K2S not only provides the sulfur insertion source, but also ignites the reaction through the formation of a trisulfur radical anion and electrons in DMF.

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Citations

Jun 21, 2019·Organic & Biomolecular Chemistry·Kunita Phakdeeyothin, Sirilata Yotphan
May 22, 2018·Chemical Communications : Chem Comm·J Vázquez, V Sindelar
Aug 14, 2021·Chemical Reviews·Xue-Qiang ChuChao-Jun Li
Aug 30, 2017·The Journal of Organic Chemistry·Qiujie TangAihua Zhou
Dec 4, 2019·Organic Letters·Peiqi ZhouHuanfeng Jiang
Dec 3, 2020·Organic Letters·Khang X NguyenNam T S Phan
Sep 21, 2021·Journal of the American Chemical Society·Shun WangBurkhard König

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Methods Mentioned

BETA
X-ray
electron paramagnetic resonance

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