Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation

Rui Sang, Peter Kucmierczyk, Ricarda Dühren, Rauf Razzaq, Kaiwu Dong, Jie Liu, Robert Franke, Ralf Jackstell, Matthias Beller

Research output: Contribution to journalReview articlepeer-review

65 Scopus citations

Abstract

The synthesis of carboxylic acids is of fundamental importance in the chemical industry and the corresponding products find numerous applications for polymers, cosmetics, pharmaceuticals, agrochemicals, and other manufactured chemicals. Although hydroxycarbonylations of olefins have been known for more than 60 years, currently known catalyst systems for this transformation do not fulfill industrial requirements, for example, stability. Presented herein for the first time is an aqueous-phase protocol that allows conversion of various olefins, including sterically hindered and demanding tetra-, tri-, and 1,1-disubstituted systems, as well as terminal alkenes, into the corresponding carboxylic acids in excellent yields. The outstanding stability of the catalyst system (26 recycling runs in 32 days without measurable loss of activity), is showcased in the preparation of an industrially relevant fatty acid. Key-to-success is the use of a built-in-base ligand under acidic aqueous conditions. This catalytic system is expected to provide a basis for new cost-competitive processes for the industrial production of carboxylic acids.

Original languageEnglish
Pages (from-to)14365-14373
Number of pages9
JournalAngewandte Chemie International Edition in English
Volume58
Issue number40
DOIs
StatePublished - 1 Oct 2019
Externally publishedYes

Keywords

  • carboxylic acids
  • industrial chemistry
  • ligand design
  • olefins
  • palladium

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