Highly Chemoselective DMPU-Mediated Trialkylsilylation of Terminal Alkynes Using Trifluoromethyltrialkylsilane

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Abstract

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.

Original languageEnglish
Pages (from-to)63-66
Number of pages4
JournalAsian Journal of Organic Chemistry
Volume6
Issue number1
DOIs
Publication statusPublished - 2017 Jan 1

Keywords

  • Ruppert–Prakash reagent
  • alkynes
  • chemoselectivity
  • silylation
  • trifluoroalkylation

ASJC Scopus subject areas

  • Organic Chemistry

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