Organic Letters 2011-05-20

Mild Pd-catalyzed N-arylation of methanesulfonamide and related nucleophiles: avoiding potentially genotoxic reagents and byproducts.

Brandon R Rosen, J Craig Ruble, Thomas J Beauchamp, Antonio Navarro

Index: Org. Lett. 13(10) , 2564-7, (2011)

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Abstract

A convenient, general, and high yielding Pd-catalyzed cross-coupling of methanesulfonamide with aryl bromides and chlorides is reported. The use of this method eliminates concern over genotoxic impurities that can arise when an aniline is reacted with methanesulfonyl chloride. The application of this method to the synthesis of dofetilide is also reported.