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Highly Chemoselective DMPU‐Mediated Trialkylsilylation of Terminal Alkynes Using Trifluoromethyltrialkylsilane
Author(s) -
NozawaKumada Kanako,
Inagi Moeto,
Kondo Yoshinori
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201600472
Subject(s) - chemistry , trifluoromethylation , deprotonation , carbene , silylation , terminal (telecommunication) , chemoselectivity , combinatorial chemistry , organic chemistry , medicinal chemistry , catalysis , trifluoromethyl , ion , telecommunications , alkyl , computer science
A chemoselective silylation of terminal alkynes with trifluoromethyltrialkylsilane in 1,3‐dimethyl‐3,4,5,6‐tetrahydro‐2(1 H )‐pyrimidinone (DMPU) is described. This process is effective even under mild conditions without the use of fluorides or an N‐heterocyclic carbene (NHC), providing a widely applicable method for the synthesis of alkynylsilicon compounds. Moreover, it was found that the preferential deprotonation of terminal alkynes using this system proceeded faster than the trifluoromethylation of aldehydes, ketones, and esters.