Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC = IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction

Steven Patrick Nolan; Frederic Izquierdo; Caroline Zinser; Yury Minenkov; David B. Cordes; Alexandra Slawin; Luigi Cavallo; Fady Nahra; Catherine S. J. Cazin

doi:10.1002/cctc.201701279

Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC = IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction

Steven Patrick Nolan, Frederic Izquierdo, Caroline Zinser, Yury Minenkov, David B. Cordes, Alexandra Slawin, Luigi Cavallo, Fady Nahra, Catherine S. J. Cazin

King Abdullah University of Science and Technology

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

26 Scopus citations

Abstract

The influence of C4,5-halogenation on palladium N-heterocyclic carbene complexes and their activity in the Suzuki-Miyaura reaction have been investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPrCl and IPrBr ligands were synthesized. After determining electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr)(cin)Cl]. The three palladium complexes were studied using DFT calculations to delineate their behaviour in the activation step leading to the putative 12-electron active catalyst. Experimentally, their catalytic activity in the Suzuki-Miyaura reaction involving a wide range of coupling partners (30 entries) at low catalyst loading was studied.

Original language	English (US)
Pages (from-to)	601-611
Number of pages	11
Journal	ChemCatChem
Volume	10
Issue number	3
DOIs	https://doi.org/10.1002/cctc.201701279
State	Published - Dec 19 2017

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10.1002/cctc.201701279

https://repository.kaust.edu.sa/bitstream/10754/625458/1/Nolan_et_al-2017-ChemCatChem.pdf

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@article{4f786f5c6a0c4df8846b0c1b54ef333c,

title = "Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC = IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction",

abstract = "The influence of C4,5-halogenation on palladium N-heterocyclic carbene complexes and their activity in the Suzuki-Miyaura reaction have been investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPrCl and IPrBr ligands were synthesized. After determining electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr)(cin)Cl]. The three palladium complexes were studied using DFT calculations to delineate their behaviour in the activation step leading to the putative 12-electron active catalyst. Experimentally, their catalytic activity in the Suzuki-Miyaura reaction involving a wide range of coupling partners (30 entries) at low catalyst loading was studied.",

author = "Nolan, {Steven Patrick} and Frederic Izquierdo and Caroline Zinser and Yury Minenkov and Cordes, {David B.} and Alexandra Slawin and Luigi Cavallo and Fady Nahra and Cazin, {Catherine S. J.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We gratefully acknowledge the European Commission (EC) for funding through the seventh framework program SYNFLOW, the European Research Council (ERC) (Advanced Investigator Award “FUNCAT” to S. P. N.), The Engineering and Physical Sciences Research Council (EPSRC) and AstraZeneca (Studentship to C. M. Z.). We thank the EPSRC National Mass Spectrometry Service Centre in Swansea for mass spectrometric analyses. We thank King Saud University and King Abdullah University of Science and Technology (Award No. OSR-2015-CCF-1974-03.)",

year = "2017",

month = dec,

day = "19",

doi = "10.1002/cctc.201701279",

language = "English (US)",

volume = "10",

pages = "601--611",

journal = "ChemCatChem",

issn = "1867-3880",

publisher = "Wiley - VCH Verlag GmbH & CO. KGaA",

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T1 - Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC = IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction

AU - Nolan, Steven Patrick

AU - Izquierdo, Frederic

AU - Zinser, Caroline

AU - Minenkov, Yury

AU - Cordes, David B.

AU - Slawin, Alexandra

AU - Cavallo, Luigi

AU - Nahra, Fady

AU - Cazin, Catherine S. J.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We gratefully acknowledge the European Commission (EC) for funding through the seventh framework program SYNFLOW, the European Research Council (ERC) (Advanced Investigator Award “FUNCAT” to S. P. N.), The Engineering and Physical Sciences Research Council (EPSRC) and AstraZeneca (Studentship to C. M. Z.). We thank the EPSRC National Mass Spectrometry Service Centre in Swansea for mass spectrometric analyses. We thank King Saud University and King Abdullah University of Science and Technology (Award No. OSR-2015-CCF-1974-03.)

PY - 2017/12/19

Y1 - 2017/12/19

N2 - The influence of C4,5-halogenation on palladium N-heterocyclic carbene complexes and their activity in the Suzuki-Miyaura reaction have been investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPrCl and IPrBr ligands were synthesized. After determining electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr)(cin)Cl]. The three palladium complexes were studied using DFT calculations to delineate their behaviour in the activation step leading to the putative 12-electron active catalyst. Experimentally, their catalytic activity in the Suzuki-Miyaura reaction involving a wide range of coupling partners (30 entries) at low catalyst loading was studied.

AB - The influence of C4,5-halogenation on palladium N-heterocyclic carbene complexes and their activity in the Suzuki-Miyaura reaction have been investigated. Two [Pd(NHC)(cin)Cl] complexes bearing IPrCl and IPrBr ligands were synthesized. After determining electronic and steric properties of these ligands, their properties were compared to those of [Pd(IPr)(cin)Cl]. The three palladium complexes were studied using DFT calculations to delineate their behaviour in the activation step leading to the putative 12-electron active catalyst. Experimentally, their catalytic activity in the Suzuki-Miyaura reaction involving a wide range of coupling partners (30 entries) at low catalyst loading was studied.

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DO - 10.1002/cctc.201701279

M3 - Article

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JO - ChemCatChem

JF - ChemCatChem

IS - 3

ER -

Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC = IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction

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CCDC 1430161: Experimental Crystal Structure Determination : (eta3-1-phenylallyl)-chloro-(4,5-dichloro-1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene)-palladium(ii)

CCDC 1430090: Experimental Crystal Structure Determination : (eta3-1-phenylallyl)-chloro-(4,5-dibromo-1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene)-palladium(ii)

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Insights into the catalytic activity of [Pd(NHC)(cin)Cl] (NHC = IPr, IPrCl, IPrBr) complexes in the Suzuki-Miyaura reaction

Abstract

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Datasets

CCDC 1430161: Experimental Crystal Structure Determination : (eta3-1-phenylallyl)-chloro-(4,5-dichloro-1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene)-palladium(ii)

CCDC 1430090: Experimental Crystal Structure Determination : (eta3-1-phenylallyl)-chloro-(4,5-dibromo-1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene)-palladium(ii)

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