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Aromatic PCN pincer palladium complexes : Forming and breaking CC bonds

Mousa, Abdelrazek H. LU ; Fleckhaus, André LU ; Kondrashov, Mikhail LU and Wendt, Ola F. LU (2017) In Journal of Organometallic Chemistry 845. p.157-164
Abstract

Through a salt metathesis reaction, ( t-BuPCN)Pd-ONO2 (2) was prepared and used as a precursor for producing ( t-BuPCN)Pd-OH (3) and ( t-BuPCN)Pd-aryl acetylide complexes 4 (phenyl acetylide) and 5 (p-tolyl acetylide). The aryl acetylide complexes could also be prepared through another synthetic route: by condensation of 3 with the corresponding aryl acetylene. The reactivity of complexes 3 and 4 toward carbon dioxide was studied and it was found that both reactions give the hydrogen carbonate complex (6). The low reactivity of the Pd-acetylide bond was further confirmed by the fact that the propiolate complex undergoes decarboxylation to give 4. PCN palladium complexes are good catalysts for... (More)

Through a salt metathesis reaction, ( t-BuPCN)Pd-ONO2 (2) was prepared and used as a precursor for producing ( t-BuPCN)Pd-OH (3) and ( t-BuPCN)Pd-aryl acetylide complexes 4 (phenyl acetylide) and 5 (p-tolyl acetylide). The aryl acetylide complexes could also be prepared through another synthetic route: by condensation of 3 with the corresponding aryl acetylene. The reactivity of complexes 3 and 4 toward carbon dioxide was studied and it was found that both reactions give the hydrogen carbonate complex (6). The low reactivity of the Pd-acetylide bond was further confirmed by the fact that the propiolate complex undergoes decarboxylation to give 4. PCN palladium complexes are good catalysts for the decarboxylative cross coupling reactions between acetylene carboxylic acids and aryl halides. The yield of the cross coupling product was improved by adding a catalytic amount of CuI.

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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Aromatic pincer complexes, Carboxylation, Decarboxylative cross coupling, Palladium, PCN pincer ligand
in
Journal of Organometallic Chemistry
volume
845
pages
157 - 164
publisher
Elsevier
external identifiers
  • scopus:85018176808
  • wos:000405773500022
ISSN
0022-328X
DOI
10.1016/j.jorganchem.2017.04.025
language
English
LU publication?
yes
id
5c765bb1-1dc7-49e6-813f-2c98e816a78b
date added to LUP
2017-05-22 11:14:35
date last changed
2018-03-11 04:40:09
@article{5c765bb1-1dc7-49e6-813f-2c98e816a78b,
  abstract     = {<p>Through a salt metathesis reaction, (<sup> t-Bu</sup>PCN)Pd-ONO<sub>2</sub> (2) was prepared and used as a precursor for producing (<sup> t-Bu</sup>PCN)Pd-OH (3) and (<sup> t-Bu</sup>PCN)Pd-aryl acetylide complexes 4 (phenyl acetylide) and 5 (p-tolyl acetylide). The aryl acetylide complexes could also be prepared through another synthetic route: by condensation of 3 with the corresponding aryl acetylene. The reactivity of complexes 3 and 4 toward carbon dioxide was studied and it was found that both reactions give the hydrogen carbonate complex (6). The low reactivity of the Pd-acetylide bond was further confirmed by the fact that the propiolate complex undergoes decarboxylation to give 4. PCN palladium complexes are good catalysts for the decarboxylative cross coupling reactions between acetylene carboxylic acids and aryl halides. The yield of the cross coupling product was improved by adding a catalytic amount of CuI.</p>},
  author       = {Mousa, Abdelrazek H. and Fleckhaus, André and Kondrashov, Mikhail and Wendt, Ola F.},
  issn         = {0022-328X},
  keyword      = {Aromatic pincer complexes,Carboxylation,Decarboxylative cross coupling,Palladium,PCN pincer ligand},
  language     = {eng},
  pages        = {157--164},
  publisher    = {Elsevier},
  series       = {Journal of Organometallic Chemistry},
  title        = {Aromatic PCN pincer palladium complexes : Forming and breaking CC bonds},
  url          = {http://dx.doi.org/10.1016/j.jorganchem.2017.04.025},
  volume       = {845},
  year         = {2017},
}