A General Method for Palladium-Catalyzed Reactions of Primary Sulfonamides with Aryl Nonaflates

Shashank Shekhar*, Travis B. Dunn*, Brian J. Kotecki, Donna K. Montavon and Steven C. Cullen

*Abbott Laboratories, Process Research and Development, 1401 Sheridan Road, North Chicago, Illinois 60064, United States, Email: shashank.shekharabbott.com, travis.dunnabbott.com

S. Shekhar, T. B. Dunn, B. J. Kotecki, D. K. Montavon, S. C. Cullen, J. Org. Chem., 2011, 76, 4552-4553.

DOI: 10.1021/jo200443u

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Abstract

A biaryl phosphine ligand, t-BuXPhos and K₃PO₄ in tert-amyl alcohol was found to be the optimal base-solvent combination for a Pd-catalyzed sulfonamidation of aryl nonafluorobutanesulfonates. The reaction conditions were tolerant of various functional groups. The only identified limitation of this methodology is the inability of 2,6-disubstituted aryl nonaflates to efficiently participate in the reaction.

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Key Words

sulfonamides, toluenesulfonamides

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ID: J42-Y2011-1600