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*

*East China University of Science & Technology, Shanghai 200237, China; University of Arizona, Tucson, Arizona 85721-0207, United States Email: xiaobeiecust.edu.cn, wwangpharmacy.arizona.edu

Z. Shen, S. Zhang, H. Geng, J. Wang, X. Zhang, A. Zhou, C. Yao, X. Chen, W. Wang, Org. Lett., 2019, 21, 448-452.

DOI: 10.1021/acs.orglett.8b03641

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Abstract

A sulfoxonium metathesis reaction between TMSOI and cost-effective DMSO-d₆ provides deuterated trimethylsulfoxonium iodide (TDMSOI). Subsequent "one-pot" trideuteromethylation installs 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.

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Key Words

ethers

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ID: J54-Y2019