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