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1,4-Aryl migration under copper(I) atom transfer conditions
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Clark, A. J. (Andrew J.), Coles, Stuart R., Collis, Alana, Debure, Thomas, Guy, Collette S., Murphy, Nicholas P. and Wilson, P. (Paul). (2009) 1,4-Aryl migration under copper(I) atom transfer conditions. Tetrahedron Letters, Vol.50 (No.40). pp. 5609-5612. ISSN 0040-4039
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Official URL: http://dx.doi.org/10.1016/j.tetlet.2009.07.089
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 > 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 |
| Date: | 7 October 2009 |
| Volume: | Vol.50 |
| Number: | No.40 |
| Number of Pages: | 4 |
| Page Range: | pp. 5609-5612 |
| Identification Number: | 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) |
| URI: | http://wrap.warwick.ac.uk/id/eprint/17307 |
Data sourced from Thomson Reuters' Web of Knowledge
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