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

Research output: Contribution to journal › Article › peer-review

81 Citations (Scopus)

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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

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

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title = "Oxidative β-C–H sulfonylation of cyclic amines",

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.\}",

year = "2018",

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doi = "10.1039/C7SC04900E",

language = "English",

journal = "Chemical Science",

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publisher = "Royal Society of Chemistry",

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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.

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

SN - 2041-6520

JO - Chemical Science

JF - Chemical Science

ER -

Oxidative β-C–H sulfonylation of cyclic amines

Abstract

Keywords

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