Oxidative β-C–H sulfonylation of cyclic amines

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...

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Bibliographic Details
Main Authors: Griffiths, RJ, Kong, WC, Richards, SA, Burley, GA, Willis, M, Talbot, EPA
Format: Journal article
Published: Royal Society of Chemistry 2018
Description
Summary: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