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

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    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.

    ORCID iDs

    Griffiths, Robert J. ORCID logoORCID: https://orcid.org/0000-0002-5692-4275, Burley, Glenn A. and Talbot, Eric P.A.;
    • Item type:Article
      ID code:60151
      Dates:
      Date
      Event
      8 February 2017
      Published
      8 February 2017
      Accepted
      Notes:This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/acs.orglett.7b00021.
      Keywords:metal-free, amine oxidation, lactams, iodine, drug scaffolds, Chemistry, Organic Chemistry
      Subjects:Science > Chemistry
      Department:Faculty of Science > Pure and Applied Chemistry
      Technology and Innovation Centre > Bionanotechnology
      Depositing user: Pure Administrator
      Date deposited:13 Mar 2017 12:26
      Last modified:23 Nov 2021 01:50
      URI:https://strathprints.strath.ac.uk/id/eprint/60151
    CORE (COnnecting REpositories)