Palladium-Catalyzed Direct Arylation of Methyl Sulfoxides with Aryl Halides
Tiezheng Jia, Ana Bellomo, Kawtar EL Baina, Spencer D. Dreher and Patrick J. Walsh*
*Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia, Pennsylvania 19104-6323, United States, Email: pwalshsas.upenn.edu
T. Jia, A. Bellomo, K. El Baina, S. D. Dreher, P. J. Walsh, J. Am. Chem. Soc., 2013, 135, 3740-3743.
DOI: 10.1021/ja4009776 (free Supporting Information)
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Deprotonation of the weakly acidic α-protons of sulfoxides with LiOtBu and the use of a palladium phosphine complex as catalyst facilitates an α-arylation of various aryl methyl sulfoxides with aryl bromides. More challenging coupling partners, such as alkyl methyl sulfoxides (including dimethyl sulfoxide) and aryl chlorides proved to be suitable under optimized conditions.
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S. Montel, T. Jia, P. J. Walsh, Org. Lett., 2014, 16, 130-133.