Visible-Light-Driven Aryl Migration and Cyclization of α-Azido Amides.

Org Lett

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China.

Published: June 2021

This paper reports two new visible-light-promoted radical reactions of α-azido amides. By catalysis of [Ir(ppy)(dtbbpy)]PF with -PrNEt as the reducing agent, -aryl α-azido tertiary amides were first converted to the corresponding aminyl radicals through reduction of the azido group; the aminyl radicals then underwent N-to-N aryl migration to give α-anilinyl-functionalized amides. α-Azido secondary amides, on the other hand, reacted with the solvent ethanol and -PrNEt to afford the imidazolinone products.

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http://dx.doi.org/10.1021/acs.orglett.1c01120DOI Listing

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