Clark, Andrew J., Coles, Stuart R., Collis, Alana, Debure, Thomas, Guy, Collette S., Murphy, Nicholas P. and Wilson, Paul (2009) 1,4-Aryl migration under copper(I) atom transfer conditions. Tetrahedron Letters, Vol.50 (No.40). pp. 5609-5612. doi:10.1016/j.tetlet.2009.07.089 ISSN 0040-4039.

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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. (C) 2009 Elsevier Ltd. All rights reserved.

Item Type:	Journal Article
Subjects:	Q Science > QD Chemistry T Technology > TP Chemical technology
Divisions:	Faculty of Science, Engineering and Medicine > Science > Chemistry
Library of Congress Subject Headings (LCSH):	Copper, Free radical reactions, Ring formation (Chemistry), Arylation
Journal or Publication Title:	Tetrahedron Letters
Publisher:	Elsevier
ISSN:	0040-4039
Official Date:	7 October 2009
Dates:	Date Event 7 October 2009 Published
Volume:	Vol.50
Number:	No.40
Number of Pages:	4
Page Range:	pp. 5609-5612
DOI:	10.1016/j.tetlet.2009.07.089
Status:	Peer Reviewed
Publication Status:	Published
Access rights to Published version:	Restricted or Subscription Access
Funder:	Engineering and Physical Sciences Research Council (EPSRC)

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