1,4-Aryl migration under copper(I) atom transfer conditions

Andrew J. Clark; Stuart R. Coles; Alana E.C. Collis; Thomas Debure; Collette S. Guy; Nicholas P. Murphy; Paul Wilson

doi:10.1016/j.tetlet.2009.07.089

1,4-Aryl migration under copper(I) atom transfer conditions

Andrew J. Clark, Stuart R. Coles, Alana E.C. Collis, Thomas Debure, Collette S. Guy, Nicholas P. Murphy, Paul Wilson

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

14 Citations (Scopus)

Abstract

Reaction of N-alkyl-N-(trichloroacetyl)arylsulfonamides with CuCl/amines leads to N-alkyl-N-(dichloroacetyl)-arylsulfonamides via reduction or N-alkyl-aryldichloroacetamides via 1,4-aryl migration with loss of SO₂. The ratio of reduction to aryl migration is dependent upon the temperature and the ligand utilised. Along with amide bond hydrolysis these reactions may compete when carrying out slow atom transfer radical cyclisation reactions using sulfonamides.

Original language	English
Pages (from-to)	5609-5612
Number of pages	4
Journal	Tetrahedron Letters
Volume	50
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2009.07.089
Publication status	Published - 7 Oct 2009
Externally published	Yes

Keywords

Aryl migration
ATRC
Copper
Radical

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10.1016/j.tetlet.2009.07.089

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title = "1,4-Aryl migration under copper(I) atom transfer conditions",

abstract = "Reaction of N-alkyl-N-(trichloroacetyl)arylsulfonamides with CuCl/amines leads to N-alkyl-N-(dichloroacetyl)-arylsulfonamides via reduction or N-alkyl-aryldichloroacetamides via 1,4-aryl migration with loss of SO2. The ratio of reduction to aryl migration is dependent upon the temperature and the ligand utilised. Along with amide bond hydrolysis these reactions may compete when carrying out slow atom transfer radical cyclisation reactions using sulfonamides.",

keywords = "Aryl migration, ATRC, Copper, Radical",

author = "Clark, {Andrew J.} and Coles, {Stuart R.} and Collis, {Alana E.C.} and Thomas Debure and Guy, {Collette S.} and Murphy, {Nicholas P.} and Paul Wilson",

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journal = "Tetrahedron Letters",

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T1 - 1,4-Aryl migration under copper(I) atom transfer conditions

AU - Clark, Andrew J.

AU - Coles, Stuart R.

AU - Collis, Alana E.C.

AU - Debure, Thomas

AU - Guy, Collette S.

AU - Murphy, Nicholas P.

AU - Wilson, Paul

PY - 2009/10/7

Y1 - 2009/10/7

N2 - Reaction of N-alkyl-N-(trichloroacetyl)arylsulfonamides with CuCl/amines leads to N-alkyl-N-(dichloroacetyl)-arylsulfonamides via reduction or N-alkyl-aryldichloroacetamides via 1,4-aryl migration with loss of SO2. The ratio of reduction to aryl migration is dependent upon the temperature and the ligand utilised. Along with amide bond hydrolysis these reactions may compete when carrying out slow atom transfer radical cyclisation reactions using sulfonamides.

AB - Reaction of N-alkyl-N-(trichloroacetyl)arylsulfonamides with CuCl/amines leads to N-alkyl-N-(dichloroacetyl)-arylsulfonamides via reduction or N-alkyl-aryldichloroacetamides via 1,4-aryl migration with loss of SO2. The ratio of reduction to aryl migration is dependent upon the temperature and the ligand utilised. Along with amide bond hydrolysis these reactions may compete when carrying out slow atom transfer radical cyclisation reactions using sulfonamides.

KW - Aryl migration

KW - ATRC

KW - Copper

KW - Radical

UR - http://www.scopus.com/inward/record.url?scp=68749113929&partnerID=8YFLogxK

U2 - 10.1016/j.tetlet.2009.07.089

DO - 10.1016/j.tetlet.2009.07.089

M3 - Article

AN - SCOPUS:68749113929

VL - 50

SP - 5609

EP - 5612

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

IS - 40

ER -

1,4-Aryl migration under copper(I) atom transfer conditions

Abstract

Keywords

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