TY - JOUR
T1 - Highly Chemoselective DMPU-Mediated Trialkylsilylation of Terminal Alkynes Using Trifluoromethyltrialkylsilane
AU - Kumada, Kanako
AU - Inagi, Moeto
AU - Kondo, Yoshinori
PY - 2017/1/1
Y1 - 2017/1/1
N2 - A chemoselective silylation of terminal alkynes with trifluoromethyltrialkylsilane in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-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.
AB - A chemoselective silylation of terminal alkynes with trifluoromethyltrialkylsilane in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-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.
KW - Ruppert–Prakash reagent
KW - alkynes
KW - chemoselectivity
KW - silylation
KW - trifluoroalkylation
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U2 - 10.1002/ajoc.201600472
DO - 10.1002/ajoc.201600472
M3 - Article
AN - SCOPUS:85008249236
VL - 6
SP - 63
EP - 66
JO - Asian Journal of Organic Chemistry
JF - Asian Journal of Organic Chemistry
SN - 2193-5807
IS - 1
ER -