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

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

doi:10.1002/cctc.201701279

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

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

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

Abstract

The influence of C^4,5-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 IPr^Cl and IPr^Br 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
Pages (from-to)	601-611
Journal	ChemCatChem
Volume	10
Issue number	3
Early online date	19 Dec 2017
DOIs	https://doi.org/10.1002/cctc.201701279
Publication status	Published - 7 Feb 2018

Keywords

Catalysis
NHC
Palladium
Suzuki-Miyaura
DFT

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10.1002/cctc.201701279

Cordes_ChemCatChem_Suzuki-Miyaura_AAM
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim. This work has been made available online in accordance with the publisher’s policies. This is the author created, accepted version manuscript following peer review and may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1002/cctc.201701279
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Cite this

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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.",

keywords = "Catalysis, NHC, Palladium, Suzuki-Miyaura, DFT",

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

note = "The authors 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.).",

year = "2018",

month = feb,

day = "7",

doi = "10.1002/cctc.201701279",

language = "English",

volume = "10",

pages = "601--611",

journal = "ChemCatChem",

issn = "1867-3899",

publisher = "Wiley-VCH, Weinheim",

number = "3",

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TY - JOUR

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

AU - Izquierdo, Frederic

AU - Zinser, Caroline

AU - Minenkov, Yury

AU - Cordes, David

AU - Slawin, Alexandra

AU - Cavallo, Luigi

AU - Nahra, Fady

AU - Cazin, Catherine

AU - Nolan, Steven Patrick

N1 - The authors 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.).

PY - 2018/2/7

Y1 - 2018/2/7

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.

KW - Catalysis

KW - NHC

KW - Palladium

KW - Suzuki-Miyaura

KW - DFT

UR - http://onlinelibrary.wiley.com/doi/10.1002/cctc.201701279/full#footer-support-info

UR - https://www.scopus.com/pages/publications/85038390467

U2 - 10.1002/cctc.201701279

DO - 10.1002/cctc.201701279

M3 - Article

SN - 1867-3899

VL - 10

SP - 601

EP - 611

JO - ChemCatChem

JF - ChemCatChem

IS - 3

ER -

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

Abstract

Keywords

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SYNFLOW 100%: SYNFLOW - 100% Contribution

FUNCAT: EU FP7 ERC Advanced Grant - FUNCAT - Fundamental Studies in Organometallic Chemistry and Homogeneous Catalysis