Synthesis of propargylic ethers by gold-mediated reaction of terminal alkynes with acetals

Miyu Furuta, Kyoko Sugiyama, Minami Yamaguchi, Hirofumi Ueda, Hidetoshi Tokuyama

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)

Abstract

A gold-catalyzed introduction of various terminal alkynes to acetals was investigated. Extensive optimization of the reaction conditions revealed that thermally stable cationic gold catalysts bearing bulky ligands such as 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene 3-1H-benzo[d][1,2,3]triazolyl gold trifluoromethanesulfonate (IPrAu(BTZ-H)OTf) were particularly suitable for the reaction. Additionally, significant solvent effects were observed. Ether solvents such as tetrahydrofuran (THF), cyclo pentyl methyl ether (CPME), and 1,4-dioxane were effective for the reaction. Studies on the scope of substrates and alkynes indicated that various alkynes and acetals were feasible to provide a wide range of propargylic ethers.

Original languageEnglish
Pages (from-to)872-876
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume67
Issue number8
DOIs
Publication statusPublished - 2019

Keywords

  • Acetal
  • Gold catalysis
  • Propargylic ether
  • Terminal alkyne

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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