Hydrocarboxylation of olefins using an amphiphilic palladium catalyst, activity and recycling properties NMR identification of some reaction intermediates

Magnus Karlsson, Adriana Ionescu, Carlaxel Andersson

Research output: Contribution to journalArticlepeer-review

14 Citations (SciVal)

Abstract

The high solubility in acidic solutions of N-bis(N',N'-diethyl-2-aminoethyl)-4-aminomethylphenyl-diphenylphosphine (N3P) make it a suitable candidate for study and comparison to the more commonly studied trisulfonated triphenylphosphine (TPPTS) ligand in the palladium catalysed aqueous hydrocarboxylation reaction. The catalyst employing N3P shows an inverted regioselectivity compared to the TPPTS system. Non-coordinating anions give the best results in terms of activity and stability of the catalyst. Due to N3P amphiphilic character and contrary to sulfonated phosphines reaction, it is possible to recycle the catalyst, both by extracting the substrate and by extracting the catalyst into an organic solvent. The hydrocarboxylation of styrene, I-octene and 4-penteneoic acid demonstrates that the reaction rate is strongly dependent on the solubility of the substrates. Using the water-soluble 3-buten-1-ol as substrate, two palladium zerovalent complexes, two palladium hydrides, one acyl and one alkyl complexes were identified by means of NMR and IR. (c) 2006 Elsevier B.V. All rights reserved.
Original languageEnglish
Pages (from-to)231-237
JournalJournal of Molecular Catalysis A: Chemical
Volume259
Issue number1-2
DOIs
Publication statusPublished - 2006

Bibliographical note

The information about affiliations in this record was updated in December 2015.
The record was previously connected to the following departments: Organic chemistry (S/LTH) (011001240), Department of Chemistry (011001220)

Subject classification (UKÄ)

  • Organic Chemistry

Keywords

  • hydrocarboxylation
  • amphiphilic phosphine
  • aqueous phase
  • palladium
  • recycling

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