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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Detalles Bibliográficos
Autores principales: Griffiths, R. J., Kong, W. C., Richards, S. A., Burley, G. A., Willis, M. C., Talbot, E. P. A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2018
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5897885/
https://www.ncbi.nlm.nih.gov/pubmed/29719703
http://dx.doi.org/10.1039/c7sc04900e
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author Griffiths, R. J.
Kong, W. C.
Richards, S. A.
Burley, G. A.
Willis, M. C.
Talbot, E. P. A.
author_facet Griffiths, R. J.
Kong, W. C.
Richards, S. A.
Burley, G. A.
Willis, M. C.
Talbot, E. P. A.
author_sort Griffiths, R. J.
collection PubMed
description 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.
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spelling pubmed-58978852018-05-01 Oxidative β-C–H sulfonylation of cyclic amines Griffiths, R. J. Kong, W. C. Richards, S. A. Burley, G. A. Willis, M. C. Talbot, E. P. A. Chem Sci Chemistry 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. Royal Society of Chemistry 2018-01-22 /pmc/articles/PMC5897885/ /pubmed/29719703 http://dx.doi.org/10.1039/c7sc04900e Text en This journal is © The Royal Society of Chemistry 2018 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Griffiths, R. J.
Kong, W. C.
Richards, S. A.
Burley, G. A.
Willis, M. C.
Talbot, E. P. A.
Oxidative β-C–H sulfonylation of cyclic amines
title Oxidative β-C–H sulfonylation of cyclic amines
title_full Oxidative β-C–H sulfonylation of cyclic amines
title_fullStr Oxidative β-C–H sulfonylation of cyclic amines
title_full_unstemmed Oxidative β-C–H sulfonylation of cyclic amines
title_short Oxidative β-C–H sulfonylation of cyclic amines
title_sort oxidative β-c–h sulfonylation of cyclic amines
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5897885/
https://www.ncbi.nlm.nih.gov/pubmed/29719703
http://dx.doi.org/10.1039/c7sc04900e
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