Oxidative β-C–H sulfonylation of cyclic amines

Griffiths, R. J. and Kong, W. C. and Richards, S. A. and Burley, G. A. and Willis, M. C. and Talbot, E. P. A. (2018) Oxidative β-C–H sulfonylation of cyclic amines. Chemical Science. ISSN 2041-6520

[img]
Preview
Text (Griffiths-etal-CS-2018-Oxidative-B-C-H-sulfonylation-of-cyclic)
Griffiths_etal_CS_2018_Oxidative_B_C_H_sulfonylation_of_cyclic.pdf
Final Published Version
License: Creative Commons Attribution-NonCommercial 4.0 logo

Download (969kB)| Preview

    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