Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer

Ze Ming Xu, Hong Xi Li, David James Young, Da Liang Zhu, Hai Yan Li, Jian Ping Lang

Research output: Contribution to journalArticle

Abstract

Visible-light-driven, intramolecular C(sp2)-H thiolation has been achieved without addition of a photosensitizer, metal catalyst, or base. This reaction induces the cyclization of thiobenzanilides to benzothiazoles. The substrate absorbs visible light, and its excited state undergoes a reverse hydrogen-atom transfer (RHAT) with 2,2,6,6-tetramethylpiperidine N-oxyl to form a sulfur radical. The addition of the sulfur radical to the benzene ring gives an aryl radical, which then rearomatizes to benzothiazole via RHAT.

Original languageEnglish
Pages (from-to)237-241
Number of pages5
JournalOrganic Letters
Volume21
Issue number1
Early online date21 Dec 2018
DOIs
Publication statusPublished - 4 Jan 2019

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