Regioselective Synthesis of 2° Amides Using Visible-Light-Induced Photoredox-Catalyzed Nonaqueous Oxidative C-N Cleavage of N,N-Dibenzylanilines

Nalladhambi Neerathilingam, Mandapati Bhargava Reddy and Ramasamy Anandhan*

*Department of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, Email: ananthanramasamygmail.com

N. Neerathilingam, M. B. Reddy, R. Anandhan, J. Org. Chem., 2021, 86, 15117-15127.

DOI: 10.1021/acs.joc.1c01792

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Abstract

A visible-light-driven photoredox-catalyzed nonaqueous oxidative C-N cleavage of N,N-dibenzylanilines provides 2° amides. The protocol also enables the conversion of 2-(dibenzylamino)benzamide to quinazolinones in the presence of (NH₄)₂S₂O₈ as an additive.

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proposed mechanism

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Key Words

amides, benzylamines, quinazolinones, oxygen, ammonium peroxydisulfate, photochemistry

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ID: J42-Y2021