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Polymer-Supported Palladium(II) Carbene Complexes : Catalytic Activity, Recyclability, and Selectivity in C-H Acetoxylation of Arenes

Majeed, Maitham H. LU ; Shayesteh, Payam LU ; Wallenberg, Lars Reine LU ; Persson, Axel R. LU orcid ; Johansson, Niclas LU ; Ye, Lei LU orcid ; Schnadt, Joachim LU orcid and Wendt, Ola F. LU (2017) In Chemistry - A European Journal 23(35). p.8457-8465
Abstract

Heterogeneous catalysts for selective oxidation of C-H bonds were synthesized by co-polymerization of new N-heterocyclic carbene-palladium(II) (NHC-PdII) monomers with divinylbenzene. The polymer-supported NHC-PdII-catalysed undirected C-H acetoxylation of simple and methylated arenes as well as polyarenes, with similar or superior efficiency compared to their homogeneous analogues. In particular, the regioselectivity has been improved in the acetoxylation of biphenyl and naphthalene compared to the best homogeneous catalysts. The new polymer-supported catalysts maintain the original oxidation state of PdII after repeated catalytic reactions, and exhibit no significant leaching of palladium. In addition,... (More)

Heterogeneous catalysts for selective oxidation of C-H bonds were synthesized by co-polymerization of new N-heterocyclic carbene-palladium(II) (NHC-PdII) monomers with divinylbenzene. The polymer-supported NHC-PdII-catalysed undirected C-H acetoxylation of simple and methylated arenes as well as polyarenes, with similar or superior efficiency compared to their homogeneous analogues. In particular, the regioselectivity has been improved in the acetoxylation of biphenyl and naphthalene compared to the best homogeneous catalysts. The new polymer-supported catalysts maintain the original oxidation state of PdII after repeated catalytic reactions, and exhibit no significant leaching of palladium. In addition, the new catalysts have been successfully recovered and reused without loss of activity over several cycles of reactions.

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author
; ; ; ; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
C-H activation, N-heterocyclic carbenes, Palladium(II), Polymer supported Pd(II), Undirected acetoxylation
in
Chemistry - A European Journal
volume
23
issue
35
pages
9 pages
publisher
Wiley-Blackwell
external identifiers
  • wos:000404009500021
  • pmid:28422334
  • scopus:85020044501
ISSN
0947-6539
DOI
10.1002/chem.201700777
language
English
LU publication?
yes
id
1547c617-13fd-49d3-a9d0-58e9399224d7
date added to LUP
2017-06-30 08:56:38
date last changed
2025-01-17 14:17:24
@article{1547c617-13fd-49d3-a9d0-58e9399224d7,
  abstract     = {{<p>Heterogeneous catalysts for selective oxidation of C-H bonds were synthesized by co-polymerization of new N-heterocyclic carbene-palladium(II) (NHC-Pd<sup>II</sup>) monomers with divinylbenzene. The polymer-supported NHC-Pd<sup>II</sup>-catalysed undirected C-H acetoxylation of simple and methylated arenes as well as polyarenes, with similar or superior efficiency compared to their homogeneous analogues. In particular, the regioselectivity has been improved in the acetoxylation of biphenyl and naphthalene compared to the best homogeneous catalysts. The new polymer-supported catalysts maintain the original oxidation state of Pd<sup>II</sup> after repeated catalytic reactions, and exhibit no significant leaching of palladium. In addition, the new catalysts have been successfully recovered and reused without loss of activity over several cycles of reactions.</p>}},
  author       = {{Majeed, Maitham H. and Shayesteh, Payam and Wallenberg, Lars Reine and Persson, Axel R. and Johansson, Niclas and Ye, Lei and Schnadt, Joachim and Wendt, Ola F.}},
  issn         = {{0947-6539}},
  keywords     = {{C-H activation; N-heterocyclic carbenes; Palladium(II); Polymer supported Pd(II); Undirected acetoxylation}},
  language     = {{eng}},
  month        = {{06}},
  number       = {{35}},
  pages        = {{8457--8465}},
  publisher    = {{Wiley-Blackwell}},
  series       = {{Chemistry - A European Journal}},
  title        = {{Polymer-Supported Palladium(II) Carbene Complexes : Catalytic Activity, Recyclability, and Selectivity in C-H Acetoxylation of Arenes}},
  url          = {{http://dx.doi.org/10.1002/chem.201700777}},
  doi          = {{10.1002/chem.201700777}},
  volume       = {{23}},
  year         = {{2017}},
}