Open AccessTrideuteromethylation Enabled by a Sulfoxonium Metathesis Reaction
Author(s) -
Zuyuan Shen,
Shilei Zhang,
Huihui Geng,
Jiarui Wang,
Xinyu Zhang,
Anqi Zhou,
Cheng Yao,
Xiaobei Chen,
Wei Wang
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.8b03641
Subject(s) - reagent , chemistry , moiety , salt metathesis reaction , metathesis , yield (engineering) , combinatorial chemistry , methylene , phenols , organic chemistry , materials science , polymerization , polymer , metallurgy
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).