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Direct Trideuteromethylation of Sulfenate Anions Generated In Situ from β-Sulfinyl Esters: An Access to Trideuteromethyl Sulfoxides

Fathima Pilathottathil, Sreelakshmi Unnikrishnan, Tamilarasu Murugesan and Alagiri Kaliyamoorthy*

*School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, Vithura, Kerala 695551, India, Email:

F. Pilathottathil, S. Unnikrishnan, T. Murugesan, A. Kaliyamoorthy, J. Org. Chem., 2023, 88, 9505-9513.

DOI: 10.1021/acs.joc.3c00573

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A direct trideuteromethylation of sulfenate ions derived in situ from β-sulfinyl esters in the presence of a base utilizing inexpensive CD3OTs as the electrophilic trideuteromethylating agent provides an array of trideuteromethyl sulfoxides in very good yields with a high degree of deuteration. Trideuteromethyl sulfoxides can be readily modified into trideuteromethyl sulfones and sulfoximines.

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Key Words


ID: J42-Y2023