Synthesis and characterization of a cationic phthalimido-functionalized N-heterocyclic carbene complex of palladium(II) and its catalytic activity

Serena L M Goh, Manuel P. Högerl, Nadežda B. Jokic̈, Alexandrina D. Tanase, Bettina Bechlars, Walter Baratta, J. Mink, Fritz E. Kühn

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Abstract

A cationic phthalimido-functionalized N-heterocyclic carbene (NHC) palladium(II) complex has been synthesized from [3-methyl-1-(2′- phthalimidoethyl)imidazolium] hexafluorophosphate ([NHCMe,PhtH] PF6) by transmetalation and isolated in 67 % yield. The title complex has been applied as catalyst in the Suzuki-Miyaura cross-coupling reaction under benign aqueous conditions. The catalyst is active without any observable initiation period. High average turnover frequencies (TOFs) of up to 55000 h-1 have been reached with catalyst concentrations as low as 0.01 mol-%. A cationic phthalimido-functionalized N-heterocyclic carbene (NHC) palladium(II) complex has been prepared in high yield. The complex was activated instantly, without an initiation period, in the Suzuki-Miyaura cross-coupling reaction under benign aqueous aerobic conditions. Turnover frequencies (TOFs) up to 55000 h-1, were achieved with 0.01 mol-% of the complex.

Original languageEnglish
Pages (from-to)1225-1230
Number of pages6
JournalEuropean Journal of Inorganic Chemistry
Issue number7
DOIs
Publication statusPublished - 2014

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Palladium
Catalyst activity
Catalysts
carbene

Keywords

  • Carbenes
  • Cross-coupling
  • Homogeneous catalysis
  • N ligands
  • Palladium

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Synthesis and characterization of a cationic phthalimido-functionalized N-heterocyclic carbene complex of palladium(II) and its catalytic activity. / Goh, Serena L M; Högerl, Manuel P.; Jokic̈, Nadežda B.; Tanase, Alexandrina D.; Bechlars, Bettina; Baratta, Walter; Mink, J.; Kühn, Fritz E.

In: European Journal of Inorganic Chemistry, No. 7, 2014, p. 1225-1230.

Research output: Contribution to journalArticle

Goh, Serena L M ; Högerl, Manuel P. ; Jokic̈, Nadežda B. ; Tanase, Alexandrina D. ; Bechlars, Bettina ; Baratta, Walter ; Mink, J. ; Kühn, Fritz E. / Synthesis and characterization of a cationic phthalimido-functionalized N-heterocyclic carbene complex of palladium(II) and its catalytic activity. In: European Journal of Inorganic Chemistry. 2014 ; No. 7. pp. 1225-1230.
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