Palladium-Catalyzed Decarboxylative Coupling of Alkynyl Carboxylic Acids with Aryl Tosylates

Ju Hyeon Lee, Gabriel Charles Edwin Raja, Subeen Yu, Junseong Lee, Kwang Ho Song, Sunwoo Lee

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4 Citations (Scopus)

Abstract

Decarboxylative coupling reactions of alkynyl carboxylic acids with aryl tosylates were developed in the presence of a palladium catalyst. Among the commercially available phosphine ligands, only 1-dicyclohexylphosphino-2-(di-tert-butylphosphino-ethyl)ferrocene (CyPF-tBu) showed good reactivity. The reaction took place smoothly and gave the decarboxylative coupled products in moderate to good yields. This demonstrates the excellent functional group tolerance toward alkyl, alkoxy, fluoro, thiophenyl, ester, and ketone groups. In addition, alkyl-substituted propiolic acids, such as octynoic and hexynoic acids, were coupled with phenyl tosylate to provide the desired products. We found that the electronic properties of the substituents on the phenyl ring in arylpropiolic acids are an important factor. The order of reactivity was found to be aryl iodide > aryl bromide > aryl tosylate > aryl chloride. However, aryl chloride-bearing electron-withdrawing groups showed higher reactivity than those bearing aryl tosylates.

Original languageEnglish
Pages (from-to)6259-6269
Number of pages11
JournalACS Omega
Volume2
Issue number9
DOIs
Publication statusPublished - 2017 Jan 1

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ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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