Trideuteromethylation Enabled by a Sulfoxonium Metathesis Reaction
| Autor: | Cheng Yao, Shen Zuyuan, Anqi Zhou, Wei Wang, Shilei Zhang, Huihui Geng, Xinyu Zhang, Jiarui Wang, Xiaobei Chen |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Extramural Chemistry Organic Chemistry 010402 general chemistry Deuterium 01 natural sciences Biochemistry Combinatorial chemistry Article 0104 chemical sciences chemistry.chemical_compound Phenols Yield (chemistry) Reagent Salt metathesis reaction Moiety Indicators and Reagents Sulfhydryl Compounds Physical and Theoretical Chemistry Methylene |
| Zdroj: | Org Lett |
| ISSN: | 1523-7052 |
| Popis: | 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). |
| Databáze: | OpenAIRE |
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