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

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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

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Inorganic Chemistry

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10.1002/ejic.201301277

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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.

@article{d0c6f5aca9a04cc3acc932453e30b0bc,

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.",

year = "2014",

month = jan,

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doi = "10.1002/ejic.201301277",

language = "English (US)",

volume = "2014",

pages = "1225--1230",

journal = "European Journal of Inorganic Chemistry",

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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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U2 - 10.1002/ejic.201301277

DO - 10.1002/ejic.201301277

M3 - Article

VL - 2014

SP - 1225

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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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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