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

doi:10.1039/C7SC04900E

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

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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

Original language	English
Number of pages	6
Journal	Chemical Science
DOIs	https://doi.org/10.1039/C7SC04900E
Publication status	Published - 22 Jan 2018

Keywords

aliphatic azacycles
drug discovery
small molecule drug discovery

Access to Document

10.1039/C7SC04900ELicence: CC BY-NC 4.0

Griffiths-etal-CS-2018-Oxidative-B-C-H-sulfonylation-of-cyclicFinal published version, 947 KBLicence: CC BY-NC 4.0

Cite this

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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",

keywords = "aliphatic azacycles, drug discovery, small molecule drug discovery",

author = "Griffiths, {R. J.} and Kong, {W. C.} and Richards, {S. A.} and Burley, {G. A.} and Willis, {M. C.} and Talbot, {E. P. A.}",

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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.

PY - 2018/1/22

Y1 - 2018/1/22

N2 - 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

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

M3 - Article

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

ER -