[PdA (IPr*) (cinnamyl)Cl]: An efficient pre-catalyst for the preparation of tetra-ortho-substituted biaryls by Suzuki-Miyaura cross-coupling

Anthony Chartoire; Mathieu Lesieur; Laura Falivene; Alexandra M. Z. Slawin; Luigi Cavallo; Catherine S. J. Cazin; Steven P. Nolan

doi:10.1002/chem.201104009

[PdA (IPr*) (cinnamyl)Cl]: An efficient pre-catalyst for the preparation of tetra-ortho-substituted biaryls by Suzuki-Miyaura cross-coupling

Anthony Chartoire, Mathieu Lesieur, Laura Falivene, Alexandra M. Z. Slawin, Luigi Cavallo, Catherine S. J. Cazin, Steven P. Nolan

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

172 Scopus citations

Abstract

The bigger the better: The new well-defined [Pd(IPr*)(cin)Cl] pre-catalyst is described (see scheme). This complex proves to be highly active in the Suzuki-Miyaura cross-coupling for the synthesis of tetra-ortho- substituted biaryls under mild conditions. IPr* is reported as the largest N-heterocyclic carbene (NHC) to date for [Pd(NHC)(cin)Cl] complexes, explaining the high reactivity observed for this complex in this challenging transformation. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Original language	English (US)
Pages (from-to)	4517-4521
Number of pages	5
Journal	Chemistry - A European Journal
Volume	18
Issue number	15
DOIs	https://doi.org/10.1002/chem.201104009
State	Published - Mar 13 2012

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: We gratefully acknowledge the EC for funding through the seventh framework programme SYNFLOW. We thank the EPSCR National Mass Spectrometry Service Center in Swansea for mass spectrometric analyses. Umicore AG is thanked for its generous gifts of materials. S.P.N. is a Royal Society Wolfson Research Merit Award holder. C.S.J.C. acknowledges the Royal Society for a University Research Fellowship.

ASJC Scopus subject areas

General Chemistry

Access to Document

10.1002/chem.201104009

Cite this

@article{c2f04c9b588949b191b1fac7fb3ef0e3,

title = "[PdA (IPr*) (cinnamyl)Cl]: An efficient pre-catalyst for the preparation of tetra-ortho-substituted biaryls by Suzuki-Miyaura cross-coupling",

abstract = "The bigger the better: The new well-defined [Pd(IPr*)(cin)Cl] pre-catalyst is described (see scheme). This complex proves to be highly active in the Suzuki-Miyaura cross-coupling for the synthesis of tetra-ortho- substituted biaryls under mild conditions. IPr* is reported as the largest N-heterocyclic carbene (NHC) to date for [Pd(NHC)(cin)Cl] complexes, explaining the high reactivity observed for this complex in this challenging transformation. {\textcopyright} 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.",

author = "Anthony Chartoire and Mathieu Lesieur and Laura Falivene and Slawin, {Alexandra M. Z.} and Luigi Cavallo and Cazin, {Catherine S. J.} and Nolan, {Steven P.}",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We gratefully acknowledge the EC for funding through the seventh framework programme SYNFLOW. We thank the EPSCR National Mass Spectrometry Service Center in Swansea for mass spectrometric analyses. Umicore AG is thanked for its generous gifts of materials. S.P.N. is a Royal Society Wolfson Research Merit Award holder. C.S.J.C. acknowledges the Royal Society for a University Research Fellowship.",

year = "2012",

month = mar,

day = "13",

doi = "10.1002/chem.201104009",

language = "English (US)",

volume = "18",

pages = "4517--4521",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "15",

}

TY - JOUR

T1 - [PdA (IPr*) (cinnamyl)Cl]: An efficient pre-catalyst for the preparation of tetra-ortho-substituted biaryls by Suzuki-Miyaura cross-coupling

AU - Chartoire, Anthony

AU - Lesieur, Mathieu

AU - Falivene, Laura

AU - Slawin, Alexandra M. Z.

AU - Cavallo, Luigi

AU - Cazin, Catherine S. J.

AU - Nolan, Steven P.

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: We gratefully acknowledge the EC for funding through the seventh framework programme SYNFLOW. We thank the EPSCR National Mass Spectrometry Service Center in Swansea for mass spectrometric analyses. Umicore AG is thanked for its generous gifts of materials. S.P.N. is a Royal Society Wolfson Research Merit Award holder. C.S.J.C. acknowledges the Royal Society for a University Research Fellowship.

PY - 2012/3/13

Y1 - 2012/3/13

N2 - The bigger the better: The new well-defined [Pd(IPr*)(cin)Cl] pre-catalyst is described (see scheme). This complex proves to be highly active in the Suzuki-Miyaura cross-coupling for the synthesis of tetra-ortho- substituted biaryls under mild conditions. IPr* is reported as the largest N-heterocyclic carbene (NHC) to date for [Pd(NHC)(cin)Cl] complexes, explaining the high reactivity observed for this complex in this challenging transformation. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

AB - The bigger the better: The new well-defined [Pd(IPr*)(cin)Cl] pre-catalyst is described (see scheme). This complex proves to be highly active in the Suzuki-Miyaura cross-coupling for the synthesis of tetra-ortho- substituted biaryls under mild conditions. IPr* is reported as the largest N-heterocyclic carbene (NHC) to date for [Pd(NHC)(cin)Cl] complexes, explaining the high reactivity observed for this complex in this challenging transformation. © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

UR - http://hdl.handle.net/10754/562127

UR - http://doi.wiley.com/10.1002/chem.201104009

UR - http://www.scopus.com/inward/record.url?scp=84859237473&partnerID=8YFLogxK

U2 - 10.1002/chem.201104009

DO - 10.1002/chem.201104009

M3 - Article

SN - 0947-6539

VL - 18

SP - 4517

EP - 4521

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 15

ER -

[PdA (IPr*) (cinnamyl)Cl]: An efficient pre-catalyst for the preparation of tetra-ortho-substituted biaryls by Suzuki-Miyaura cross-coupling

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

CCDC 857933: Experimental Crystal Structure Determination : (eta^3^-1-Phenylallyl)-chloro-(1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)-palladium benzene solvate

Cite this

[PdA (IPr*) (cinnamyl)Cl]: An efficient pre-catalyst for the preparation of tetra-ortho-substituted biaryls by Suzuki-Miyaura cross-coupling

Abstract

Bibliographical note

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 857933: Experimental Crystal Structure Determination : (eta^3^-1-Phenylallyl)-chloro-(1,3-bis(2,6-bis(diphenylmethyl)-4-methylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene)-palladium benzene solvate

Cite this