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Oxidative ?-C-H sulfonylation of cyclic amines.

ABSTRACT: A transition metal-free strategy for the dehydrogenative ?-sulfonylation of tertiary cyclic amines is described. N-Iodosuccinimide facilitates regioselective oxidative sulfonylation at C-H bonds positioned ? 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.

SUBMITTER: Griffiths RJ

PROVIDER: S-EPMC5897885 | biostudies-other | 2018 Feb

REPOSITORIES: biostudies-other

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Oxidative β-C-H sulfonylation of cyclic amines.

Griffiths R J RJ Kong W C WC Richards S A SA Burley G A GA Willis M C MC Talbot E P A EPA

Chemical science 20180122 8

A transition metal-free strategy for the dehydrogenative β-sulfonylation of tertiary cyclic amines is described. <i>N</i>-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 ...[more]

PMID: 29719703

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