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Methanesulfinylation of Benzyl Halides with Dimethyl Sulfoxide

Duo Fu, Jun Dong, Hongguang Du and Jiaxi Xu*

*Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People's Republic of China, Email:

D. Fu, J. Dong, H. Du, J. Xu, J. Org. Chem., 2020, 85, 2752-2758.

DOI: 10.1021/acs.joc.9b03041


A phenyltrimethylammonium tribromide-mediated nucleophilic substitution/oxygen transformation reaction of benzyl halides with DMSO enables a convenient and direct synthesis of various benzyl methyl sulfoxides. In this transition-metal-free reaction, DMSO acts as not only a solvent but also a "S(O)Me" source.

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ID: J42-Y2020