文献类型：期刊文献

英文题名：Trideuteromethylation Enabled by a Sulfoxonium Metathesis Reaction

作者：Shen, Zuyuan[1,2];Zhang, Shilei[3,4];Geng, Huihui[1,2];Wang, Jiarui[1,2];Zhang, Xinyu[1,2];Zhou, Anqi[1,2];Yao, Cheng[1,2];Chen, Xiaobei[1,2];Wang, Wei[1,2,5,6]

机构：[1]East China Univ Sci & Technol, State Key Lab Bioengn Reactor, Sch Pharm, Shanghai 200237, Peoples R China;[2]East China Univ Sci & Technol, Shanghai Key Lab New Drug Design, Sch Pharm, Shanghai 200237, Peoples R China;[3]Soochow Univ, Jiangsu Key Lab Neuropsychiat Dis, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China;[4]Soochow Univ, Coll Pharmaceut Sci, 199 Renai Rd, Suzhou 215123, Jiangsu, Peoples R China;[5]Univ Arizona, Dept Pharmacol & Toxicol, 1703 East Mabel St,POB 210207, Tucson, AZ 85721 USA;[6]Univ Arizona, BIO5 Inst, 1703 East Mabel St,POB 210207, Tucson, AZ 85721 USA

年份：2019

卷号：21

期号：2

起止页码：448

外文期刊名：ORGANIC LETTERS

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000456633000021)，CCR-EXPANDED(收录号:WOS:000456633000021)】；

基金：Financial support of this research from the program of the National Natural Science Foundation of China (21572055 and 21738002, W.W., and 21702058, X.C.) and the National Institutes of Health (1R01GM125920-01, W.W.) is gratefully acknowledged.

语种：英文

摘要：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 -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).