期刊
ACS CATALYSIS
卷 7, 期 4, 页码 2730-2734出版社
AMER CHEMICAL SOC
DOI: 10.1021/acscatal.7b00426
关键词
electrochemistry; radicals; benzothiazole; TEMPO; cyclization
资金
- MOST [2016YFA0204100]
- NSFC [21402164, 21672178, 21603227]
- Thousand Youth Talents Plan
- XMU
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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