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 (free Supporting Information)
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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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