Synlett 2016; 27(01): 101-105
DOI: 10.1055/s-0035-1560578
letter
© Georg Thieme Verlag Stuttgart · New York

One-Pot Sulfonamide Synthesis Exploiting the Palladium-Catalyzed Sulfination of Aryl Iodides

Emmanuel Ferrer Flegeau, Jack M. Harrison, Michael C. Willis*
  • Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK   Email: michael.willis@chem.ox.ac.uk
Further Information

Publication History

Received: 10 September 2015

Accepted: 25 September 2015

Publication Date:
13 October 2015 (eFirst)

Dedicated, with best wishes, to Professor Steven Ley on the occasion of his 70th birthday

Abstract

Aryl ammonium sulfinates, conveniently prepared from aryl iodides and the sulfur dioxide surrogate DABSO, under the action of a palladium(0) catalyst, are transformed in a one-pot process to a variety of functionalized sulfonamides. The sulfinate to sulfonamide transformation is achieved by simple treatment with an aqueous solution of the relevant amine and sodium hypochlorite (bleach). A broad range of amines, including anilines, and amino acid derivatives, are combined efficiently with a variety of aryl iodides, leading to sulfonamides in high yields.

Supporting Information