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Organophotoredox-Catalyzed Cross-Dehydrogenative Sulfonamidation of Indoles and Other Heterocycles

Aditya Paul, Arunava Sengupta and Somnath Yadav*

*Department of Chemistry and Chemical Biology, Indian Institute of Technology (ISM), Dhanbad, Jharkhand 826004, India, Email: somnathiitism.ac.in

A. Paul, A. Sengupta, S. Yadav, J. Org. Chem., 2023, 88, 9599-9614.

DOI: 10.1021/acs.joc.2c02022


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Abstract

Visible light mediates an operationally simple and regioselective synthesis of 2-sulfonamidoindoles and other 2-sulfonamido heteroarenes by an oxidative cross-dehydrogenative coupling of indoles (heteroarenes) with di-p-toluenesulfonamide or N-aryl-p-toluenesulfonamides in the presence of eosin-Y. The reaction enables the synthesis of a wide range of amidated heterocyclic compounds.


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proposed mechanism



Key Words

indoles, photochemistry, PIDA


ID: J42-Y2023