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Issue 8, 2018
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Oxidative β-C–H sulfonylation of cyclic amines

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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.

Graphical abstract: Oxidative β-C–H sulfonylation of cyclic amines

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Publication details

The article was received on 14 Nov 2017, accepted on 19 Jan 2018 and first published on 22 Jan 2018


Article type: Edge Article
DOI: 10.1039/C7SC04900E
Citation: Chem. Sci., 2018,9, 2295-2300
  • Open access: Creative Commons BY-NC license
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    Oxidative β-C–H sulfonylation of cyclic amines

    R. J. Griffiths, W. C. Kong, S. A. Richards, G. A. Burley, M. C. Willis and E. P. A. Talbot, Chem. Sci., 2018, 9, 2295
    DOI: 10.1039/C7SC04900E

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