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

Handle URI:
http://hdl.handle.net/10754/563359
Title:
Synthesis and characterization of a cationic phthalimido-functionalized N-heterocyclic carbene complex of palladium(II) and its catalytic activity
Authors:
Goh, Li Min Serena; Hogerl, Manuel Peter; Jokic̈, Nadežda B.; Tanase, Alexandrina D.; Bechlars, Bettina; Baratta, Walter; Mínk, János; Kühn, Fritz
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.
KAUST Department:
KAUST Catalysis Center (KCC); Chemical Science Program
Publisher:
Wiley-Blackwell
Journal:
European Journal of Inorganic Chemistry
Issue Date:
29-Jan-2014
DOI:
10.1002/ejic.201301277
Type:
Article
ISSN:
14341948
Sponsors:
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.
Is Supplemented By:
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:http://hdl.handle.net/10754/624629
Appears in Collections:
Articles; Chemical Science Program; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorGoh, Li Min Serenaen
dc.contributor.authorHogerl, Manuel Peteren
dc.contributor.authorJokic̈, Nadežda B.en
dc.contributor.authorTanase, Alexandrina D.en
dc.contributor.authorBechlars, Bettinaen
dc.contributor.authorBaratta, Walteren
dc.contributor.authorMínk, Jánosen
dc.contributor.authorKühn, Fritzen
dc.date.accessioned2015-08-03T11:46:38Zen
dc.date.available2015-08-03T11:46:38Zen
dc.date.issued2014-01-29en
dc.identifier.issn14341948en
dc.identifier.doi10.1002/ejic.201301277en
dc.identifier.urihttp://hdl.handle.net/10754/563359en
dc.description.abstractA 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.en
dc.description.sponsorshipThe 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.en
dc.publisherWiley-Blackwellen
dc.subjectCarbenesen
dc.subjectCross-couplingen
dc.subjectHomogeneous catalysisen
dc.subjectN ligandsen
dc.subjectPalladiumen
dc.titleSynthesis and characterization of a cationic phthalimido-functionalized N-heterocyclic carbene complex of palladium(II) and its catalytic activityen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.contributor.departmentChemical Science Programen
dc.identifier.journalEuropean Journal of Inorganic Chemistryen
dc.contributor.institutionMolecular Catalysis, Catalysis Research Center, Technische Universität München, Lichtenbergstr. 4, 85747 Garching b. Munchen, Germanyen
dc.contributor.institutionDepartment of Inorganic Chemistry, Department of Chemistry, Technische Universität München, Lichtenbergstr. 4, 85747 Garching b. Munchen, Germanyen
dc.contributor.institutionDipartimento di Chimica, Fisica e Ambiente, Università di Udine, Via Cotonificio 108, 33100 Udine, Italyen
dc.contributor.institutionStructural Chemistry Department, Institute of Chemistry, Chemical Research Center of the Hungarian Academy of Sciences, Pusztaszeri út 59-67, 1025 Budapest, Hungaryen
dc.contributor.institutionDepartment of Analytical Chemistry, University of Veszprém, P. O. Box 158, 8201 Veszprem, Hungaryen
dc.contributor.institutionAnalytical Chemistry Research Group of the Hungarian Academy of Sciences, University of Veszprém, P. O. Box 158, 8201 Veszprem, Hungaryen
kaust.authorGoh, Li Min Serenaen
kaust.authorHogerl, Manuel Peteren
dc.relation.isSupplementedByGoh, 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/ccw2g4jen
dc.relation.isSupplementedByDOI:10.5517/ccw2g4jen
dc.relation.isSupplementedByHANDLE:http://hdl.handle.net/10754/624629en
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