1,4-Aryl migration under copper(I) atom transfer conditions

Andrew J. Clark, Stuart R. Coles, Alana E.C. Collis, Thomas Debure, Collette S. Guy, Nicholas P. Murphy, Paul Wilson

Research output: Contribution to journalArticleResearchpeer-review

9 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)5609-5612
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number40
DOIs
Publication statusPublished - 7 Oct 2009
Externally publishedYes

Keywords

  • Aryl migration
  • ATRC
  • Copper
  • Radical

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