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Trideuteromethylation Enabled by a Sulfoxonium Metathesis Reaction

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journal contribution
posted on 07.01.2019, 19:21 by Zuyuan Shen, Shilei Zhang, Huihui Geng, Jiarui Wang, Xinyu Zhang, Anqi Zhou, Cheng Yao, Xiaobei Chen, Wei Wang
A conceptually novel sulfoxonium metathesis reaction between TMSOI and cost-effective DMSO-d6 is developed for the efficient generation of a new trideuteromethylation reagent TDMSOI. The new reagent TDMSOI is produced highly efficiently by simply heating a mixture of TMSOI and DMSO-d6 and directly used for subsequent trideuteromethylation in a “one-pot” operation. The preparative power of the new versatile reagent and the “one-pot” protocol is demonstrated by its use to install the −CD3 moiety into broad functionalities including phenols, thiophenols, acidic amines, and enolizable methylene units in high yield and at a useful level of deuteration (>87% D).