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.
see article for more reactions
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.
see article for more examples
H. Jiang, T. Jia, M. Zhang, P. J. Walsh, Org. Lett., 2016, 18, 972-975.