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Org Lett. 2016 Apr 01;18(7):1646-9. doi: 10.1021/acs.orglett.6b00512. Epub 2016 Mar 23.

Benzylic C-H Azidation Using the Zhdankin Reagent and a Copper Photoredox Catalyst.

Organic letters

Pauline T G Rabet, Gabriele Fumagalli, Scott Boyd, Michael F Greaney

Affiliations

  1. School of Chemistry, University of Manchester , Oxford Road, Manchester M13 9PL, U.K.
  2. Department of Oncology, AstraZeneca , Alderley Park, Macclesfield SK10 4TG, U.K.

PMID: 27007454 DOI: 10.1021/acs.orglett.6b00512

Abstract

An azidation method for C-N bond formation at benzylic C-H positions is described using copper-catalyzed visible light photochemistry and the Zhdankin azidoiodinane reagent. The method is applicable to a wide range of substrates bearing different functional groups and having a primary, secondary, or tertiary benzylic position, and is thought to proceed through a radical chain reaction.

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