Functionalization of alkynes catalyzed by t-Bu-P4 base

Tatsushi Imahori, Chieko Hori, Yoshinori Kondo

Research output: Contribution to journalArticlepeer-review

75 Citations (Scopus)

Abstract

The addition of O- and N-nucleophiles to alkynes catalyzed by a phosphazene base, t-Bu-P4 base, was investigated. Alkynes were easily transformed to enol ethers and enamines in DMSO by the addition of nucleophiles. When phenylacetylene was reacted with diisopropylamine, a unique head-to-head dimerization of phenylacetylene was observed to give the enyne derivative. Terminal proton of phenylacetylene was also catalytically activated by t-Bu-P4 base to generate the acetylide anion which was reacted with carbonyl compounds to give phenylpropargylic alcohol derivatives.

Original languageEnglish
Pages (from-to)1090-1092
Number of pages3
JournalAdvanced Synthesis and Catalysis
Volume346
Issue number9-10
DOIs
Publication statusPublished - 2004 Aug 1

Keywords

  • Alkynes
  • Enamines
  • Nucleophilic addition
  • Organic catalysis
  • Phosphazenes
  • Propargyl alcohols

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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