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 journalArticleResearchpeer-review

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.

LanguageEnglish
Pages237-241
Number of pages5
JournalOrganic Letters
Volume21
Issue number1
Early online date21 Dec 2018
DOIs
Publication statusPublished - 4 Jan 2019

Fingerprint

Photosensitizing Agents
Sulfur
Hydrogen
hydrogen atoms
Benzothiazoles
Metals
Light
Atoms
Cyclization
sulfur
Benzene
Excited states
metals
Catalysts
Substrates
benzene
catalysts
rings
excitation
benzothiazole

Cite this

Xu, Ze Ming ; Li, Hong Xi ; Young, David James ; Zhu, Da Liang ; Li, Hai Yan ; Lang, Jian Ping. / Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer. In: Organic Letters. 2019 ; Vol. 21, No. 1. pp. 237-241.
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Exogenous Photosensitizer-, Metal-, and Base-Free Visible-Light-Promoted C-H Thiolation via Reverse Hydrogen Atom Transfer. / Xu, Ze Ming; Li, Hong Xi; Young, David James; Zhu, Da Liang; Li, Hai Yan; Lang, Jian Ping.

In: Organic Letters, Vol. 21, No. 1, 04.01.2019, p. 237-241.

Research output: Contribution to journalArticleResearchpeer-review

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