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

Karlsson, Magnus ; Ionescu, Adriana LU and Andersson, Carlaxel LU (2006) In Journal of Molecular Catalysis A: Chemical 259(1-2). p.231-237
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... (More)
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. (Less)
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publication status
published
subject
keywords
hydrocarboxylation, amphiphilic phosphine, aqueous phase, palladium, recycling
in
Journal of Molecular Catalysis A: Chemical
volume
259
issue
1-2
pages
231 - 237
publisher
Elsevier
external identifiers
  • wos:000241924100036
  • scopus:33750130594
ISSN
1381-1169
DOI
10.1016/j.molcata.2006.06.036
language
English
LU publication?
yes
additional info
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)
id
a10f97e4-b426-4a60-b0fd-f389be9589d5 (old id 376957)
date added to LUP
2016-04-01 16:54:47
date last changed
2021-05-25 02:28:56
@article{a10f97e4-b426-4a60-b0fd-f389be9589d5,
  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.},
  author       = {Karlsson, Magnus and Ionescu, Adriana and Andersson, Carlaxel},
  issn         = {1381-1169},
  language     = {eng},
  number       = {1-2},
  pages        = {231--237},
  publisher    = {Elsevier},
  series       = {Journal of Molecular Catalysis A: Chemical},
  title        = {Hydrocarboxylation of olefins using an amphiphilic palladium catalyst, activity and recycling properties NMR identification of some reaction intermediates},
  url          = {http://dx.doi.org/10.1016/j.molcata.2006.06.036},
  doi          = {10.1016/j.molcata.2006.06.036},
  volume       = {259},
  year         = {2006},
}