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.willischem.ox.ac.uk

E. F. Flegeau, J. M. Harrison, M. C. Willis, Synlett, 2016, 27, 101-105.

DOI: 10.1055/s-0035-1560578

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Abstract

A Pd-catalyzed coupling of aryl iodides and the sulfur dioxide surrogate DABSO provides aryl ammonium sulfinates, that can be transformed in a one-pot process to various functionalized sulfonamides 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 can be used.

see article for more examples

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DABCO-Bis(sulfur dioxide), DABSO, as a Convenient Source of Sulfur Dioxide for Organic Synthesis: Utility in Sulfonamide and Sulfamide Preparation

H. Woolven, C. Gonzáles-Rodríguez, I. Marco, A. L. Thompson, M. C. Willis, Org. Lett., 2011, 13, 4876-4878.

DABSO-Based, Three-Component, One-Pot Sulfone Synthesis

A. S. Deeming, C. J. Russell, A. J. Henessy, M. C. Willis, Org. Lett., 2014, 16, 150-153.

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Key Words

sulfonamides (arylation, amination), palladium catalysis, sulfinates, sulfinic acids, amines, aryl halides, bleach

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ID: J60-Y2016