Transition-Metal-Free Amine Oxidation: A Chemoselective Strategy for the Late-Stage Formation of Lactams

Robert J. Griffiths, Glenn A. Burley* and Eric P. A. Talbot*

*University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL; GlaxoSmithKline Medicines Research Centre, Stevenage, Hertfordshire SG1 2NY, U.K., Email: glenn.burleystrath.ac.uk, eric.talbotpharmaron-uk.com

R. J. Griffiths, G. A. Burley, E. P. A. Talbot, Org. Lett., 2017, 19, 870-873.

DOI: 10.1021/acs.orglett.7b00021

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Abstract

In a metal-free, selective oxidation of cyclic secondary and tertiary amines for the formation of lactams, molecular iodine facilitates both chemoselective and regioselective oxidation of C-H bonds directly adjacent to a cyclic amine. The reaction offers mild conditions, functional group tolerance, and a broad substrate scope.

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Key Words

δ-lactams, ε-lactams, oxidation, iodine

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ID: J54-Y2017