Coupling reactions of alkynylsilanes mediated by a Cu(I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes

Yasushi Nishihara, Kazutaka Ikegashira, Kazunori Hirabayashi, Jun Ichi Ando, Atsunori Mori, Tamejiro Hiyama

Research output: Contribution to journalArticle

242 Citations (Scopus)

Abstract

Reaction of 1-trimethylsilylalkyne with copper(I) chloride in a polar solvent, DMF, at 60 °C under an aerobic conditions smoothly undergoes homo- coupling to give the corresponding symmetrical 1,3-butadiynes in 70-99% yields. In addition, (arylethynyl)trimethylsilanes are found to couple with aryl triflates and chlorides in the presence of Cu(I)/Pd(0) (10 mol %/5 or 10 mol %) cocatalyst system to give the corresponding diarylethynes in 49-99% yields. The cross-coupling reaction is applied to a one-pot synthesis of the corresponding unsymmetrical diarylethynes from (trimethylsilyl)ethyne via sequential Sonogashira-Hagihara and the present cross-coupling reactions using two different aryl triflates. The reactions of (arylethynyl)trimethylsilanes with aryl(chloro)ethynes in the presence of 10 mol % of CuCl also yield the corresponding unsymmetrical 1,3-butadiynes in 43-97% yields.

Original languageEnglish
Pages (from-to)1780-1787
Number of pages8
JournalJournal of Organic Chemistry
Volume65
Issue number6
DOIs
Publication statusPublished - Mar 24 2000
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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