Aromatic PCN pincer palladium complexes: forming and breaking C[sbnd]C bonds

Abdelrazek H. Mousa, André Fleckhaus, Mikhail Kondrashov, Ola F. Wendt*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

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 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.

Original languageEnglish
Pages (from-to)157-164
Number of pages8
JournalJournal of Organometallic Chemistry
Volume845
DOIs
StatePublished - 2017
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2017 Elsevier B.V.

Keywords

  • Aromatic pincer complexes
  • Carboxylation
  • Decarboxylative cross coupling
  • Palladium
  • PCN pincer ligand

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry
  • Materials Chemistry

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