Oxidative β-C–H sulfonylation of cyclic amines

R. J. Griffiths, W. C. Kong, S. A. Richards, G. A. Burley, M. C. Willis, E. P. A. Talbot

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Abstract

A transition metal-free strategy for the dehydrogenative β-sulfonylation of tertiary cyclic amines is described. N-iodosuccinimide facilitates regioselective oxidative sulfonylation at C–H bonds positioned β to the nitrogen atom of tertiary amines, installing enaminyl sulfone functionality in cyclic systems. Mild reaction conditions, broad functional group tolerance and a wide substrate scope are demonstrated. The nucleophilic character of the enaminyl sulfone is harnessed, demonstrating potential application for scaffold diversification
Original languageEnglish
Number of pages6
JournalChemical Science
DOIs
Publication statusPublished - 22 Jan 2018

Keywords

  • aliphatic azacycles
  • drug discovery
  • small molecule drug discovery

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  • Cite this

    Griffiths, R. J., Kong, W. C., Richards, S. A., Burley, G. A., Willis, M. C., & Talbot, E. P. A. (2018). Oxidative β-C–H sulfonylation of cyclic amines. Chemical Science. https://doi.org/10.1039/C7SC04900E