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

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

doi:10.1002/ejic.201301277

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

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

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

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.

Original language	English (US)
Pages (from-to)	1225-1230
Number of pages	6
Journal	European Journal of Inorganic Chemistry
Volume	2014
Issue number	7
DOIs	https://doi.org/10.1002/ejic.201301277
State	Published - Jan 29 2014

ASJC Scopus subject areas

Inorganic Chemistry

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CCDC 806717: Experimental Crystal Structure Determination : bis(acetonitrile)-chloro-(1-(2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl)-3-methylimidazol-2-ylidene)-palladium hexafluorophosphate acetonitrile solvate
Goh, S. L. M. (Creator), Hogerl, M. P. (Creator), Jokić, N. B. (Creator), Tanase, A. D. (Creator), Bechlars, B. (Creator), Baratta, W. (Creator), Mink, J. (Creator), Kühn, F. E. (Creator), Goh, S. L. M. (Creator), Jokić, N. B. (Creator), Tanase, A. D. (Creator), Bechlars, B. (Creator), Baratta, W. (Creator), Mink, J. (Creator) & Kühn, F. E. (Creator), Cambridge Crystallographic Data Centre, Mar 28 2014
DOI: 10.5517/ccw2g4j, http://hdl.handle.net/10754/624629
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Goh, Li Min Serena ; Hogerl, Manuel Peter ; Jokic̈, Nadežda B. ; Tanase, Alexandrina D. ; Bechlars, Bettina ; Baratta, Walter ; Mínk, János ; Kühn, Fritz. / 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 ; Vol. 2014, No. 7. pp. 1225-1230.

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

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 {\textcopyright} 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

author = "Goh, {Li Min Serena} and Hogerl, {Manuel Peter} and Joki{\"c}, {Nade{\v z}da B.} and Tanase, {Alexandrina D.} and Bettina Bechlars and Walter Baratta and J{\'a}nos M{\'i}nk and Fritz K{\"u}hn",

note = "KAUST Repository Item: Exported on 2020-10-01 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.",

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Synthesis and characterization of a cationic phthalimido-functionalized N-heterocyclic carbene complex of palladium(II) and its catalytic activity. / Goh, Li Min Serena; Hogerl, Manuel Peter; Jokic̈, Nadežda B.; Tanase, Alexandrina D.; Bechlars, Bettina; Baratta, Walter; Mínk, János; Kühn, Fritz.

In: European Journal of Inorganic Chemistry, Vol. 2014, No. 7, 29.01.2014, p. 1225-1230.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis and characterization of a cationic phthalimido-functionalized N-heterocyclic carbene complex of palladium(II) and its catalytic activity

AU - Goh, Li Min Serena

AU - Hogerl, Manuel Peter

AU - Jokic̈, Nadežda B.

AU - Tanase, Alexandrina D.

AU - Bechlars, Bettina

AU - Baratta, Walter

AU - Mínk, János

AU - Kühn, Fritz

N1 - KAUST Repository Item: Exported on 2020-10-01 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.

PY - 2014/1/29

Y1 - 2014/1/29

N2 - 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.

AB - 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.

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DO - 10.1002/ejic.201301277

M3 - Article

VL - 2014

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EP - 1230

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

SN - 1434-1948

IS - 7

ER -

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

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CCDC 806717: Experimental Crystal Structure Determination : bis(acetonitrile)-chloro-(1-(2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl)-3-methylimidazol-2-ylidene)-palladium hexafluorophosphate acetonitrile solvate

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