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

Type
Article

Authors
Goh, Li Min Serena
Hogerl, Manuel Peter
Jokic̈, Nadežda B.
Tanase, Alexandrina D.
Bechlars, Bettina
Baratta, Walter
Mínk, János
Kühn, Fritz

KAUST Department
KAUST Catalysis Center (KCC)
Chemical Science Program

Online Publication Date
2014-01-29

Print Publication Date
2014-03

Date
2014-01-29

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. Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Citation
Goh, S. L. M., Högerl, M. P., Jokić, N. B., Tanase, A. D., Bechlars, B., Baratta, W., … Kühn, F. E. (2014). Synthesis and Characterization of a Cationic Phthalimido-Functionalized N-Heterocyclic Carbene Complex of Palladium(II) and Its Catalytic Activity. European Journal of Inorganic Chemistry, 2014(7), 1225–1230. doi:10.1002/ejic.201301277

Acknowledgements
The Bayerische Forschungsstiftung is acknowledged for a Ph. D. grant to S. L. M. G., Wacker Insitut fur Silicium Chemie at TUM, Wacker AG is acknowledged for a Ph. D. grant to M. P. H., Universitat Bayern e. V. is acknowledged for a Ph. D. fellowship to N. B. J., and the Bavarian Elite Network NanoCat is acknowledged for a Ph. D. fellowship to A. D. T. The International Graduate School of Science and Engineering (IGSSE) and the Technische Universitat Munchen Graduate School are acknowledged for additional financial support.

Publisher
Wiley

Journal
European Journal of Inorganic Chemistry

DOI
10.1002/ejic.201301277

Relations
Is Supplemented By:
  • [Dataset]
    Goh, S. L. M., Högerl, M. P., Jokić, N. B., Tanase, A. D., Bechlars, B., Baratta, W., … Kühn, F. E. (2014). CCDC 806717: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/ccw2g4j. DOI: 10.5517/ccw2g4j HANDLE: 10754/624629

Permanent link to this record
http://hdl.handle.net/10754/563359
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