Trideuteromethylation Enabled by a Sulfoxonium Metathesis Reaction

Zuyuan Shen, Shilei Zhang, Huihui Geng, Jiarui Wang, Xinyu Zhang, Anqi Zhou, Cheng Yao, Xiaobei Chen, Wei Wang

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

A conceptually novel sulfoxonium metathesis reaction between TMSOI and cost-effective DMSO-d 6 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-d 6 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 ?CD 3 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).

Original languageEnglish (US)
Pages (from-to)448-452
Number of pages5
JournalOrganic Letters
Volume21
Issue number2
DOIs
StatePublished - Jan 18 2019

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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