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

Deuterated organic molecules have immense value in the pharmaceutical industry. Here, we present a synthetic strategy for direct trideuteromethylation of sulfenate ions derived in situ from β-sulfinyl esters in the presence of a base utilizing inexpensive and abundant CD 3 OTs as the electrophilic trideuteromethylating agent. This protocol provides straightforward access to an array of trideuteromethyl sulfoxides in yields of 75-92% with a high degree of deuteration. The ensuing trideuteromethyl sulfoxide can be readily modified into trideuteromethyl sulfone and sulfoximine.