Photo-induced 1,2-thiohydroxylation of maleimide involving disulfide and singlet oxygen

Tamanna Khandelia; Subhendu Ghosh; Pritishree Panigrahi; Raju Mandal; Deepjyoti Boruah; Bhisma K. Patel

doi:10.1039/D3CC03296E

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Photo-induced 1,2-thiohydroxylation of maleimide involving disulfide and singlet oxygen†

Tamanna Khandelia,

^a Subhendu Ghosh,

^a Pritishree Panigrahi,

^a Raju Mandal,

^a Deepjyoti Boruah

^a and Bhisma K. Patel

*^a

Author affiliations

* Corresponding authors

^a Department of Chemistry, Indian Institute of Technology Guwahati, Assam, India
E-mail: patel@iitg.ac.in
Fax: +91-3612690762

Abstract

A visible light-driven di-functionalization of maleimide with disulfide and in situ-generated singlet oxygen offers selective 1,2-thiohydroxylation under additive-free conditions. Here the disulfide plays the dual role of photosensitizer and the coupling reagent. Notably, the hydroxyl functionality originates from the in situ generated singlet oxygen followed by HAT from H₂O (moisture).

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DOI: https://doi.org/10.1039/D3CC03296E
Article type: Communication
Submitted: 08 Jul 2023
Accepted: 24 Aug 2023
First published: 24 Aug 2023

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Chem. Commun., 2023,59, 11196-11199

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Photo-induced 1,2-thiohydroxylation of maleimide involving disulfide and singlet oxygen

T. Khandelia, S. Ghosh, P. Panigrahi, R. Mandal, D. Boruah and B. K. Patel, Chem. Commun., 2023, 59, 11196 DOI: 10.1039/D3CC03296E

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Chemical Communications

Photo-induced 1,2-thiohydroxylation of maleimide involving disulfide and singlet oxygen†

Abstract

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Photo-induced 1,2-thiohydroxylation of maleimide involving disulfide and singlet oxygen

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