Transition-metal-free amine oxidation : a chemoselective strategy for the late-stage formation of lactams

Griffiths, Robert J. and Burley, Glenn A. and Talbot, Eric P.A. (2017) Transition-metal-free amine oxidation : a chemoselective strategy for the late-stage formation of lactams. Organic Letters, 19 (4). pp. 870-873. ISSN 1523-7060

[img]
Preview
Text (Griffiths-etal-OL-2017-Transition-metal-free-amine-oxidation)
Griffiths_etal_OL_2017_Transition_metal_free_amine_oxidation.pdf
Accepted Author Manuscript

Download (8MB)| Preview

    Abstract

    A metal-free strategy for the formation of lactams via selective oxidation of cyclic secondary and tertiary amines is described. Molecular iodine facilitates both chemoselective and regioselective oxidation of C–H bonds directly adjacent to a cyclic amine. The mild conditions, functional group tolerance, and substrate scope are demonstrated using a suite of diverse small molecule cyclic amines, including clinically approved drug scaffolds.