Benzothiazole Synthesis: Mechanistic Investigation of an in Situ-Generated Photosensitizing Disulfide

Ho Seong Hwang, Sumin Lee, Sung Su Han, Yu Kyung Moon, Youngmin You, Eun Jin Cho

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

The use of a visible light absorbing intermediate as a photosensitizer makes a chemical process simple and sustainable, obviating the need for the use of chemical additives. Herein, the formation of a photosensitizing disulfide in benzothiazole synthesis from 2-Aminothiophenol and aldehydes was proposed and confirmed through in-depth mechanistic studies. A series of photophysical and electrochemical investigations revealed that an in situ-generated disulfide photosensitizes molecular oxygen to generate the key oxidants, singlet oxygen and superoxide anion, for the dehydrogenation step.

Original languageEnglish
Pages (from-to)11835-11843
Number of pages9
JournalJournal of Organic Chemistry
Volume85
Issue number18
DOIs
StatePublished - 18 Sep 2020

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Copyright © 2020 American Chemical Society.

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