Highly-efficient and recyclable nanosized MCM-41 anchored palladium bipyridyl complex-catalyzed coupling of acyl chlorides and terminal alkynes for the formation of ynones

Jun You Chen, Tze Chiao Lin, Szu Chien Chen, Ai Jan Chen, Chung Yuan Mou, Fu Yu Tsai

Research output: Contribution to journalArticlepeer-review

41 Citations (Scopus)

Abstract

A highly-efficient and practical method for the formation of ynones from a variety of acyl chlorides and terminal alkynes catalyzed by a nanosized MCM-41 anchored palladium bipyridyl complex is described herein. Aroyl, heteroaroyl, and alkyl acyl chlorides were easily coupled with terminal alkynes, giving good to high isolated yields in the presence of a very low catalyst loading (0.002-0.1 mol % Pd) in Et3N or diisopropylethylamine at 50 °C. Furthermore, the reaction scale was up to 150 mmol for a single batch reaction, providing the potential for practically synthetic application. After centrifugation, the supported catalyst was able to be recycled and reused several times with only a slight decrease in activity.

Original languageEnglish
Pages (from-to)10134-10141
Number of pages8
JournalTetrahedron
Volume65
Issue number49
DOIs
Publication statusPublished - Dec 5 2009
Externally publishedYes

Keywords

  • Acyl chloride
  • Mesoporous silica
  • Palladium bipyridyl complex
  • Recyclable catalyst
  • Ynone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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