催化作用
电化学
化学
组合化学
有机化学
电极
物理化学
作者
Xiangyang Qian,Shu-Qi Li,Jinshuai Song,Hai-Chao Xu
标识
DOI:10.1021/acscatal.7b00426
摘要
Benzothiazoles and thiazolopyridines are widely prevalent in pharmaceuticals and organic materials. Herein, we report a metal- and reagent-free method for the uniform synthesis of benzothiazoles and thiazolopyridines through 2,2,6,6-tetramethylpiperidine-N-oxyl radical (TEMPO)-catalyzed electrolytic C–H thiolation. This dehydrogenative coupling process provides access to a host of benzothiazoles and thiazolopyridines from N-(hetero)arylthioamides. Mechanistic studies suggested that the thioamide substrate was oxidized with the electrochemically generated TEMPO+ through an inner-sphere electron transfer to afford a thioamidyl radical, which undergoes homolytic aromatic substitution to form the key C–S bond.
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