Palladium-catalyzed carbonylation of aryl halides - A detailed investigation of the alkoxycarbonylation of 4-bromoacetophenone

Wolfgang Mägerlein, Matthias Beller, Adriano F. Indolese

Research output: Contribution to journalArticlepeer-review

63 Scopus citations

Abstract

The palladium-catalyzed alkoxycarbonylation of 4-bromoacetophenone with n-butanol to give the corresponding benzoic acid ester has been studied systematically by evaluating the influence of critical reaction parameters such as temperature, CO pressure, solvent, base, catalyst precursor and ligand/palladium ratio. The highest catalyst efficiency was displayed at 130°C and low CO pressures using the neat alcohol as the solvent, a trialkylamine as the base and Pd(PPh3)4 or a PdCl2(PhCN)2/n PPh3- combination as the catalyst precursor. A strong dependence of the catalyst activity and stability on the phosphine concentration in the reaction mixture was found as demonstrated by the time/conversion behavior of the reaction. Thus, under the optimized conditions, catalyst productivities (turnover number = TON) of up to 7000 (70% yield of 2) were achieved. (C) 2000 Elsevier Science B.V.

Original languageEnglish
Pages (from-to)213-221
Number of pages9
JournalJournal of Molecular Catalysis A: Chemical
Volume156
Issue number1-2
DOIs
StatePublished - 20 May 2000
Externally publishedYes

Keywords

  • Aromatic carboxylic acid esters
  • Carbonylation
  • Homogeneous catalysis
  • Palladium

Fingerprint

Dive into the research topics of 'Palladium-catalyzed carbonylation of aryl halides - A detailed investigation of the alkoxycarbonylation of 4-bromoacetophenone'. Together they form a unique fingerprint.

Cite this