A versatile and efficient palladium-meta-terarylphosphine catalyst for the copper-free sonogashira coupling of (hetero-)aryl chlorides and alkynes

Yong Yang, Xinying Chew, Charles W. Johannes, Edward G. Robins, Howard Jong, Yee Hwee Lim

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

A novel meta-terarylphosphine ligand, Cy∗Phine, was developed and found to be a highly active promoter of copper-free Sonogashira cross-coupling reactions when combined in situ with a palladium source. The evolutionary m-terarylphosphine ligand architecture was able to impose significant performance advantages over its biarylphosphine congeners. An expedient and versatile protocol was also devised with an emphasis on substrates applicable to the fine-chemicals industry by featuring a diverse range of challenging, electronrich aryl chlorides and terminal alkynes. The Pd-Cy∗Phine catalyst was able to deliver products in excellent yields with efficient substrate utilization, which minimizes the generation of commonly formed byproducts, and the reaction is tolerant of a variety of substrates with unprotected functional groups.

Original languageEnglish
Pages (from-to)7184-7192
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number32
DOIs
Publication statusPublished or Issued - 24 Sept 2014
Externally publishedYes

Keywords

  • Alkynes
  • C-c coupling
  • Cross-coupling
  • Palladium
  • Phosphane ligands
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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