2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides

Andrew J. Clark, Stuart R. Coles, Alana E.C. Collis, David R. Fullaway, Nicholas P. Murphy, Paul Wilson

Research output: Contribution to journalArticleResearchpeer-review

16 Citations (Scopus)

Abstract

Reaction of N-alkyl-N-arylsulfonyl-2-halo-propionamides with pentamethyldiethylenetriamine and either CuBr or CuCl leads to 2-aryl propionamides via initial radical generation, 1,4-aryl migration with loss of SO2 and reduction of the intermediate amidyl radical in 40-99% yields.

Original languageEnglish
Pages (from-to)6311-6314
Number of pages4
JournalTetrahedron Letters
Volume50
Issue number46
DOIs
Publication statusPublished - 18 Nov 2009
Externally publishedYes

Keywords

  • Aryl migration
  • Atom transfer
  • ATRC
  • Copper
  • Dimethylpiperazine
  • Radical

Cite this

Clark, A. J., Coles, S. R., Collis, A. E. C., Fullaway, D. R., Murphy, N. P., & Wilson, P. (2009). 2-Aryl propionamides via 1,4-aryl radical migration from N-arylsulfonyl-2-bromopropionamides. Tetrahedron Letters, 50(46), 6311-6314. https://doi.org/10.1016/j.tetlet.2009.08.125