Photocatalytic Visible-Light-Induced Nitrogen Insertion via Dual C(sp³)-H and C(sp²)-H Bond Functionalization: Access to Privileged Imidazole-based Scaffolds

Srilaxmi M. Patel, Ermiya Prasad P., Manickam Bakthadoss* and Duddu S. Sharada*

*Pondicherry University, Puducherry 605 014; Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana 502 285, India, Email: bhakthadossyahoo.com, sharadachy.iith.ac.in

S. M. Patel, E. Prasad P., M. Bakthadoss, D. S. Sharada, Org. Lett., 2021, 23, 257-261.

DOI: 10.1021/acs.orglett.0c03269

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Abstract

A visible-light-mediated metal-free organic-dye-catalyzed dehydrogenative N-insertion provides highly substituted imidazoles and privileged dihydroisoquinoline-based imidazole derivatives. This sustainable, convenient, metal-free azidation/C-H aminative cyclization approach works without oxidants via a photoinduced iminyl radical as key intermediate for the nitrogen insertion.

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Key Words

imidazoles, photochemistry

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ID: J54-Y2021