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

Deuterated organic molecules have immense value in thepharmaceuticalindustry. Here, we present a synthetic strategy for direct trideuteromethylationof sulfenate ions derived in situ from beta-sulfinyl esters inthe presence of a base utilizing inexpensive and abundant CD3OTs as the electrophilic trideuteromethylating agent. This protocolprovides straightforward access to an array of trideuteromethyl sulfoxidesin yields of 75-92% with a high degree of deuteration. Theensuing trideuteromethyl sulfoxide can be readily modified into trideuteromethylsulfone and sulfoximine.

Automated summary

In this study, a synthetic strategy for direct trideuteromethylation of sulfenate ions derived from beta-sulfinyl esters in the presence of a base using CD3OTs was developed. The method allows for the straightforward synthesis of trideuteromethyl sulfoxides with high yields and deuteration levels. The resulting trideuteromethyl sulfoxide can be easily modified into trideuteromethyl sulfone and sulfoximine.