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

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

*School of Chemistry, University of Manchester, Oxford Road, Manchester M13 9PL, U.K., Email: michael.greaneymanchester.ac.uk

P. T. G. Rabet, G. Fumagalli, S. Boyd, M. F. Greaney, Org. Lett., 2016, 18, 1645-1649.

DOI: 10.1021/acs.orglett.6b00512 (free Supporting Information)


Abstract

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

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Key Words

benzyl azides


ID: J54-Y2016