Oxidative β-C–H sulfonylation of cyclic amines

R. J. Griffiths, W. C. Kong, S. A. Richards, G. A. Burley, M. C. Willis, E. P. A. Talbot

Research output: Contribution to journalArticle

18 Citations (Scopus)

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
LanguageEnglish
Number of pages6
JournalChemical Science
DOIs
Publication statusPublished - 22 Jan 2018

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Sulfones
Amines
Scaffolds
Functional groups
Transition metals
Nitrogen
Atoms
Substrates
N-iodosuccinimide

Keywords

  • aliphatic azacycles
  • drug discovery
  • small molecule drug discovery

Cite this

Griffiths, R. J., Kong, W. C., Richards, S. A., Burley, G. A., Willis, M. C., & Talbot, E. P. A. (2018). Oxidative β-C–H sulfonylation of cyclic amines. Chemical Science. https://doi.org/10.1039/C7SC04900E
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. In: Chemical Science. 2018.
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Griffiths, RJ, Kong, WC, Richards, SA, Burley, GA, Willis, MC & Talbot, EPA 2018, 'Oxidative β-C–H sulfonylation of cyclic amines' Chemical Science. https://doi.org/10.1039/C7SC04900E

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.

In: Chemical Science, 22.01.2018.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Oxidative β-C–H sulfonylation of cyclic amines

AU - Griffiths, R. J.

AU - Kong, W. C.

AU - Richards, S. A.

AU - Burley, G. A.

AU - Willis, M. C.

AU - Talbot, E. P. A.

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AB - 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

KW - aliphatic azacycles

KW - drug discovery

KW - small molecule drug discovery

U2 - 10.1039/C7SC04900E

DO - 10.1039/C7SC04900E

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Griffiths RJ, Kong WC, Richards SA, Burley GA, Willis MC, Talbot EPA. Oxidative β-C–H sulfonylation of cyclic amines. Chemical Science. 2018 Jan 22. https://doi.org/10.1039/C7SC04900E