Hexafluorosilicic Acid as a Novel Reagent for the Desilylation of Silylacetylenes: Application in Sequential Sonogashira Coupling and Click Reaction

Ádám Sinai, Ádám Mészáros, Ádám Balogh, Márton Zwillinger, Z. Novák

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7 Citations (Scopus)

Abstract

Hexafluorosilicic acid was utilized as a novel, cheap, readily available, and environmentally benign alternative reagent for the desilylation of 1-trimethylsilylacetylenes. The applicability of the aqueous solution of the hexafluorosilicic acid was demonstrated in the sequential coupling of aryl halides and ethynyltrimethylsilane to afford internal acetylenes, benzofurans, and triazoles in one-pot Sonogashira-Sonogashira­ and Sonogashira-CuAAC reactions.

Original languageEnglish
Article numberss-2017-z1879-fa
Pages (from-to)2374-2388
Number of pages15
JournalSynthesis (Germany)
Volume49
Issue number11
DOIs
Publication statusPublished - Jun 1 2017

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Keywords

  • alkynes
  • azides
  • click reaction
  • cross-coupling­
  • cycloaddition
  • fluoride
  • heterocycles
  • palladium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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