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Directed C-H Halogenation Reactions Catalysed by PdII Supported on Polymers under Batch and Continuous Flow Conditions

Majeed, Maitham H LU ; Shayesteh, Payam LU ; Tunå, Per LU ; Persson, Axel R LU ; Gritcenko, Roman LU ; Wallenberg, L Reine LU ; Ye, Lei LU ; Hulteberg, Christian LU ; Schnadt, Joachim LU and Wendt, Ola F LU (2019) In Chemistry (Weinheim an der Bergstrasse, Germany) 25(59). p.13591-13597
Abstract

A new generation of N-heterocyclic carbene palladium(II) complexes containing vinyl groups in different positions in the backbone of the N-heterocycle have been developed. The fully characterised monomers were copolymerised with divinylbenzene to fabricate robust polymer supported NHC-PdII complexes and these polymers were applied as heterogeneous catalysts in directed C-H halogenation of arenes with a pyridine-type directing group. The catalysts demonstrated medium-high catalytic activity with up to 90 % conversion and 100 % selectivity in chlorination. They are heterogeneous and recyclable (at least six times) with no significant leaching of palladium in batch mode catalysis. The best catalyst was also applied under continuous flow... (More)

A new generation of N-heterocyclic carbene palladium(II) complexes containing vinyl groups in different positions in the backbone of the N-heterocycle have been developed. The fully characterised monomers were copolymerised with divinylbenzene to fabricate robust polymer supported NHC-PdII complexes and these polymers were applied as heterogeneous catalysts in directed C-H halogenation of arenes with a pyridine-type directing group. The catalysts demonstrated medium-high catalytic activity with up to 90 % conversion and 100 % selectivity in chlorination. They are heterogeneous and recyclable (at least six times) with no significant leaching of palladium in batch mode catalysis. The best catalyst was also applied under continuous flow conditions where it disclosed an exceptional activity (90 % conversion) and 100 % selectivity for the mono-halogenated product for at least six days, with no leaching of palladium, no loss of activity and an ability to maintain the original oxidation state of PdII .

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Chemistry (Weinheim an der Bergstrasse, Germany)
volume
25
issue
59
pages
13591 - 13597
publisher
Wiley Online Library
external identifiers
  • scopus:85073662662
  • pmid:31418957
ISSN
1521-3765
DOI
10.1002/chem.201902949
language
English
LU publication?
yes
additional info
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
id
64a52dcd-0b29-43d5-a9ee-d93b4c06672e
date added to LUP
2019-09-23 13:10:46
date last changed
2020-01-18 02:20:23
@article{64a52dcd-0b29-43d5-a9ee-d93b4c06672e,
  abstract     = {<p>A new generation of N-heterocyclic carbene palladium(II) complexes containing vinyl groups in different positions in the backbone of the N-heterocycle have been developed. The fully characterised monomers were copolymerised with divinylbenzene to fabricate robust polymer supported NHC-PdII complexes and these polymers were applied as heterogeneous catalysts in directed C-H halogenation of arenes with a pyridine-type directing group. The catalysts demonstrated medium-high catalytic activity with up to 90 % conversion and 100 % selectivity in chlorination. They are heterogeneous and recyclable (at least six times) with no significant leaching of palladium in batch mode catalysis. The best catalyst was also applied under continuous flow conditions where it disclosed an exceptional activity (90 % conversion) and 100 % selectivity for the mono-halogenated product for at least six days, with no leaching of palladium, no loss of activity and an ability to maintain the original oxidation state of PdII .</p>},
  author       = {Majeed, Maitham H and Shayesteh, Payam and Tunå, Per and Persson, Axel R and Gritcenko, Roman and Wallenberg, L Reine and Ye, Lei and Hulteberg, Christian and Schnadt, Joachim and Wendt, Ola F},
  issn         = {1521-3765},
  language     = {eng},
  number       = {59},
  pages        = {13591--13597},
  publisher    = {Wiley Online Library},
  series       = {Chemistry (Weinheim an der Bergstrasse, Germany)},
  title        = {Directed C-H Halogenation Reactions Catalysed by PdII Supported on Polymers under Batch and Continuous Flow Conditions},
  url          = {http://dx.doi.org/10.1002/chem.201902949},
  doi          = {10.1002/chem.201902949},
  volume       = {25},
  year         = {2019},
}