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

Authors :: Clark, Andrew J.
Coles, Stuart R.
Collis, Alana
Debure, Thomas
Guy, Collette
Murphy, Nicholas P.
Wilson, Paul
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Oct2009, Vol. 50 Issue 40, p5609-5612. 4p.
Publication Year :: 2009
Abstract: 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. [Copyright &y& Elsevier]

Subjects :: *COPPER compounds
*SULFONAMIDES
*AMINES
*CHEMICAL reduction
*ACETAMIDE
*LIGANDS (Chemistry)
*RING formation (Chemistry)

Language :: English
ISSN :: 00404039
Volume :: 50
Issue :: 40
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 43870731
Full Text :: https://doi.org/10.1016/j.tetlet.2009.07.089