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1,4-Aryl migration under copper(I) atom transfer conditions
Authors:Andrew J Clark  Stuart R Coles  Alana Collis  Thomas Debure  Collette Guy  Nicholas P Murphy  Paul Wilson
Institution:aDepartment of Chemistry, University of Warwick, Coventry, West Midlands CV4 7AL, UK
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:Copper  ATRC  Radical  Aryl migration
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