Palladium-Catalyzed Arylation of Alkyl Sulfenate Anions

Tiezheng Jia, Mengnan Zhang, Hui Jiang, Carol Y. Wang and Patrick J. Walsh*

*Department of Chemistry, University of Pennsylvania, 231 S. 34th St., Philadelphia, Pennsylvania 19104-6323, United States, Email: pwalshsas.upenn.edu

T. Jia, M. Zhang, H. Jiang, C. Y. Wang, P. J. Walsh, J. Am. Chem. Soc., 2015, 137, 13887-13893.

DOI: 10.1021/jacs.5b08117

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Abstract

A fluoride triggered elimination strategy with alkyl 2-(trimethylsilyl)ethyl sulfoxides enables a unique palladium-catalyzed arylation of alkyl sulfenate anions to provide aryl alkyl sulfoxides in high yields. Due to the base sensitivity of the starting sulfoxides, intermediates, and products, the use of a mild method to generate alkyl sulfenate anions was crucial to the success of this process.

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Palladium-Catalyzed Arylation of Aryl Sulfenate Anions with Aryl Bromides under Mild Conditions: Synthesis of Diaryl Sulfoxides

H. Jiang, T. Jia, M. Zhang, P. J. Walsh, Org. Lett., 2016, 18, 972-975.

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Key Words

arylation

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ID: J48-Y2015