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KOtBu-Promoted Halogen-Bond-Assisted Intramolecular C-S Cross-Coupling of o-Iodothioanilides for the Synthesis of 2-Substituted Benzothiazoles

Anuradha Nandy and Govindasamy Sekar*

*Department of Chemistry, Indian Institute of Technology Madras, Chennai, Tamil Nadu 600 036, India, Email: gsekariitm.ac.in

A. Nandy, G. Sekar, J. Org. Chem., 2021, 86, 15825-15834.

DOI: 10.1021/acs.joc.1c02023 (free Supporting Information)


Abstract

KOtBu promotes a mild intramolecular C-S cross-coupling of ortho-iodothioanilides in the presence of a catalytic amount of phenanthroline as an additive for the convenient synthesis of a wide variety of 2-alkyl- and 2-aryl-substituted benzothiazoles in excellent yields.


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proposed mechanism



Key Words

benzothiazoles


ID: J42-Y2021