2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides

Andrew J. Clark; Stuart R. Coles; Alana E.C. Collis; David R. Fullaway; Nicholas P. Murphy; Paul Wilson

doi:10.1016/j.tetlet.2009.08.125

2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides

Andrew J. Clark, Stuart R. Coles, Alana E.C. Collis, David R. Fullaway, Nicholas P. Murphy, Paul Wilson

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

19 Citations (Scopus)

Abstract

Reaction of N-alkyl-N-arylsulfonyl-2-halo-propionamides with pentamethyldiethylenetriamine and either CuBr or CuCl leads to 2-aryl propionamides via initial radical generation, 1,4-aryl migration with loss of SO₂ and reduction of the intermediate amidyl radical in 40-99% yields.

Original language	English
Pages (from-to)	6311-6314
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	46
DOIs	https://doi.org/10.1016/j.tetlet.2009.08.125
Publication status	Published - 18 Nov 2009
Externally published	Yes

Keywords

Aryl migration
Atom transfer
ATRC
Copper
Dimethylpiperazine
Radical

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10.1016/j.tetlet.2009.08.125

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title = "2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides",

abstract = "Reaction of N-alkyl-N-arylsulfonyl-2-halo-propionamides with pentamethyldiethylenetriamine and either CuBr or CuCl leads to 2-aryl propionamides via initial radical generation, 1,4-aryl migration with loss of SO2 and reduction of the intermediate amidyl radical in 40-99% yields.",

keywords = "Aryl migration, Atom transfer, ATRC, Copper, Dimethylpiperazine, Radical",

author = "Clark, {Andrew J.} and Coles, {Stuart R.} and Collis, {Alana E.C.} and Fullaway, {David R.} and Murphy, {Nicholas P.} and Paul Wilson",

year = "2009",

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day = "18",

doi = "10.1016/j.tetlet.2009.08.125",

language = "English",

volume = "50",

pages = "6311--6314",

journal = "Tetrahedron Letters",

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T1 - 2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides

AU - Clark, Andrew J.

AU - Coles, Stuart R.

AU - Collis, Alana E.C.

AU - Fullaway, David R.

AU - Murphy, Nicholas P.

AU - Wilson, Paul

PY - 2009/11/18

Y1 - 2009/11/18

N2 - Reaction of N-alkyl-N-arylsulfonyl-2-halo-propionamides with pentamethyldiethylenetriamine and either CuBr or CuCl leads to 2-aryl propionamides via initial radical generation, 1,4-aryl migration with loss of SO2 and reduction of the intermediate amidyl radical in 40-99% yields.

AB - Reaction of N-alkyl-N-arylsulfonyl-2-halo-propionamides with pentamethyldiethylenetriamine and either CuBr or CuCl leads to 2-aryl propionamides via initial radical generation, 1,4-aryl migration with loss of SO2 and reduction of the intermediate amidyl radical in 40-99% yields.

KW - Aryl migration

KW - Atom transfer

KW - ATRC

KW - Copper

KW - Dimethylpiperazine

KW - Radical

UR - http://www.scopus.com/inward/record.url?scp=70349484802&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2009.08.125

DO - 10.1016/j.tetlet.2009.08.125

M3 - Article

AN - SCOPUS:70349484802

VL - 50

SP - 6311

EP - 6314

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 46

ER -

2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides

Abstract

Keywords

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