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

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

*Division of Chemical Engineering and Materials Science, Ewha Womans University, Seoul 03760, Republic of Korea, Email: odds2ewha.ac.kr, ejchocau.ac.kr

H. S. Hwang, S. Lee, S. S. Han, Y. K. Moon, Y. You, E. J. Cho, J. Org. Chem., 2020, 85, 11835-11843.

DOI: 10.1021/acs.joc.0c01598 (free Supporting Information)


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Abstract

In a visible light mediated synthesis of benzothiazoles from 2-aminothiophenol and aldehydes, an in situ-generated disulfide photosensitizes molecular oxygen to generate the key oxidants, singlet oxygen and superoxide anion, for the dehydrogenation step.


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proposed reaction pathway



Key Words

benzothiazoles, oxygen, photochemistry


ID: J42-Y2020