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Visible Light-Induced Decomposition of Acyl Peroxides Using Isocyanides: Synthesis of Heteroarenes by Radical Cascade Cyclization

Navin Yadav, Sushil Ranjan Bhatta and Jarugu Narasimha Moorthy*

*Department of Chemistry, Indian Institute of Technology, Kanpur, Uttar Pradesh 208016, India, Email: moorthyiitk.ac.in

N. Yadav, S. R. Bhatta, J. N. Moorthy, J. Org. Chem., 2023, 88, 5431-5439.

DOI: 10.1021/acs.joc.2c03059


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Abstract

Visible light mediates facile syntheses of isoquinolines, benzothiazoles, and quinazolines from isocyanides and inexpensive acyl peroxides. Singlet-excited isocyanides decompose acyl peroxides into aryl/alkyl radicals. The latter attack the isocyanides, yielding imidoyl radicals that subsequently cyclize to afford heteroarene products.

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proposed mechanism



Key Words

isoquinolines, benzothiazoles, photochemistry


ID: J42-Y2023