Oxidative β-C-H sulfonylation of cyclic aminesElectronic supplementary information (ESI) available. See DOI: 10.1039/c7sc04900e

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 cycli...

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Bibliographic Details
Main Authors: Griffiths, R. J, Kong, W. C, Richards, S. A, Burley, G. A, Willis, M. C, Talbot, E. P. A
Format: Article
Language:English
Online Access:Get full text
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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. A new and efficient process to access β-functionalisation of cyclic amines via a mild oxidative β-sulfonylation.
ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc04900e