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

doi:10.1021/acs.orglett.8b03641

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

Pharmacology and Toxicology

Research output: Contribution to journal › Article › peer-review

38 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 language	English (US)
Pages (from-to)	448-452
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	2
DOIs	https://doi.org/10.1021/acs.orglett.8b03641
State	Published - Jan 18 2019

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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).",

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T1 - Trideuteromethylation Enabled by a Sulfoxonium Metathesis Reaction

AU - Shen, Zuyuan

AU - Zhang, Shilei

AU - Geng, Huihui

AU - Wang, Jiarui

AU - Zhang, Xinyu

AU - Zhou, Anqi

AU - Yao, Cheng

AU - Chen, Xiaobei

AU - Wang, Wei

PY - 2019/1/18

Y1 - 2019/1/18

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AB - 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).

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Trideuteromethylation Enabled by a Sulfoxonium Metathesis Reaction

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