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Riboflavin as Photoredox Catalyst in the Cyclization of Thiobenzanilides: Synthesis of 2-Substituted Benzothiazoles

Lydia M. Bouchet, Adrián A. Heredia, Juan E. Argüello* and Luciana C. Schmidt*

*Departamento de Química Orgánica, Facultad de Ciencias Químicas, Universidad Nacional de Córdoba, Ciudad Universitaria, X5000HUA Córdoba, Argentina, Email: jeafcq.unc.edu.ar, lucianafcq.unc.edu.ar

L. M. Bouchet, A. A. Heredia, J. E. Argüello, L. C. Schmidt, Org. Lett., 2020, 22, 610-614.

DOI: 10.1021/acs.orglett.9b04384 (free Supporting Information)


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Abstract

Visible light mediates a transition-metal-free formation of benzothiazoles from thiobenzanilides in the presence of riboflavin as a photosensitizer and potassium peroxydisulfate as a sacrificial oxidizing agent. This methodology tolerates a broad range of functional groups and affords 2-substituted benzothiazoles in good yields under very mild conditions.

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Key Words

benzothiazoles, photochemistry, potassium peroxydisulfate


ID: J54-Y2020