1,4-Aryl migration under copper(I) atom transfer conditions
- Clark, Andrew J.
- Coles, Stuart R.
- Collis, Alana
- Debure, Thomas
- Guy, Collette S.
- Murphy, Nicholas P.
- Wilson, Paul
Publication date
October 2009
DOI Publisher
Elsevier BV ISSN
0040-4039 Citation count (estimate)
11Abstract
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
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