Versatile relay and cooperative palladium(0) N-heterocyclic carbene/copper(I) N-heterocyclic carbene catalysis for the synthesis of tri- and tetrasubstituted alkenes

Mathieu Lesieur; Yannick Daniel Bidal; Faima Lazreg; Fady Nahra; Catherine S.J. Cazin

doi:10.1002/cctc.201500268

Versatile relay and cooperative palladium(0) N-heterocyclic carbene/copper(I) N-heterocyclic carbene catalysis for the synthesis of tri- and tetrasubstituted alkenes

Mathieu Lesieur, Yannick Daniel Bidal, Faima Lazreg, Fady Nahra, Catherine S.J. Cazin

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

Abstract

Two new and efficient dual catalytic procedures for the synthesis of tri- and tetra-substituted alkenes using aryl bromides and chlorides are reported. The formation of these vinyl arenes occurs independently in a one-pot relay and a one-pot cooperative procedure using well-defined Pd-NHC and Cu-NHC complexes. Mechanistic studies were performed to elucidate the key role of the solvent in each procedure as well as the formation of the key intermediate, [Cu(alkenylboron)(NHC)], allowing the transmetallation with the Pd-NHC co-catalyst in the cooperative catalysis.

Original language	English
Pages (from-to)	2108–2112
Journal	ChemCatChem
Volume	7
Issue number	14
Early online date	26 Jun 2015
DOIs	https://doi.org/10.1002/cctc.201500268
Publication status	Published - 13 Jul 2015

Keywords

Alkenes
Copper
Palladium
N-heterocyclic
Carbene
Dual catalysis

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10.1002/cctc.201500268

Cazin_2015_CCC_Versatile_AM
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This is the accepted version of the following article: Lesieur, M., Bidal, Y. D., Lazreg, F., Nahra, F. and Cazin, C. S. J. (2015), Versatile Relay and Cooperative Palladium(0) N-Heterocyclic Carbene/Copper(I) N-Heterocyclic Carbene Catalysis for the Synthesis of Tri- and Tetrasubstituted Alkenes. ChemCatChem, 7: 2108–2112, which has been published in final form at https://dx.doi.org/10.1002/cctc.201500268
Accepted author manuscript, 756 KB

Cite this

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title = "Versatile relay and cooperative palladium(0) N-heterocyclic carbene/copper(I) N-heterocyclic carbene catalysis for the synthesis of tri- and tetrasubstituted alkenes",

abstract = "Two new and efficient dual catalytic procedures for the synthesis of tri- and tetra-substituted alkenes using aryl bromides and chlorides are reported. The formation of these vinyl arenes occurs independently in a one-pot relay and a one-pot cooperative procedure using well-defined Pd-NHC and Cu-NHC complexes. Mechanistic studies were performed to elucidate the key role of the solvent in each procedure as well as the formation of the key intermediate, [Cu(alkenylboron)(NHC)], allowing the transmetallation with the Pd-NHC co-catalyst in the cooperative catalysis.",

keywords = "Alkenes, Copper, Palladium, N-heterocyclic, Carbene, Dual catalysis",

author = "Mathieu Lesieur and Bidal, {Yannick Daniel} and Faima Lazreg and Fady Nahra and Cazin, {Catherine S.J.}",

note = "The authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC) for financial support. We also thank the EPSCR National Mass Spectrometry Service Centre in Swansea for the High Resolution Mass Spectrometry and Umicore for the generous gift of palladium starting materials. ",

year = "2015",

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day = "13",

doi = "10.1002/cctc.201500268",

language = "English",

volume = "7",

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T1 - Versatile relay and cooperative palladium(0) N-heterocyclic carbene/copper(I) N-heterocyclic carbene catalysis for the synthesis of tri- and tetrasubstituted alkenes

AU - Lesieur, Mathieu

AU - Bidal, Yannick Daniel

AU - Lazreg, Faima

AU - Nahra, Fady

AU - Cazin, Catherine S.J.

N1 - The authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC) for financial support. We also thank the EPSCR National Mass Spectrometry Service Centre in Swansea for the High Resolution Mass Spectrometry and Umicore for the generous gift of palladium starting materials.

PY - 2015/7/13

Y1 - 2015/7/13

N2 - Two new and efficient dual catalytic procedures for the synthesis of tri- and tetra-substituted alkenes using aryl bromides and chlorides are reported. The formation of these vinyl arenes occurs independently in a one-pot relay and a one-pot cooperative procedure using well-defined Pd-NHC and Cu-NHC complexes. Mechanistic studies were performed to elucidate the key role of the solvent in each procedure as well as the formation of the key intermediate, [Cu(alkenylboron)(NHC)], allowing the transmetallation with the Pd-NHC co-catalyst in the cooperative catalysis.

AB - Two new and efficient dual catalytic procedures for the synthesis of tri- and tetra-substituted alkenes using aryl bromides and chlorides are reported. The formation of these vinyl arenes occurs independently in a one-pot relay and a one-pot cooperative procedure using well-defined Pd-NHC and Cu-NHC complexes. Mechanistic studies were performed to elucidate the key role of the solvent in each procedure as well as the formation of the key intermediate, [Cu(alkenylboron)(NHC)], allowing the transmetallation with the Pd-NHC co-catalyst in the cooperative catalysis.

KW - Alkenes

KW - Copper

KW - Palladium

KW - N-heterocyclic

KW - Carbene

KW - Dual catalysis

UR - http://onlinelibrary.wiley.com/doi/10.1002/cctc.201500268/suppinfo

U2 - 10.1002/cctc.201500268

DO - 10.1002/cctc.201500268

M3 - Article

SN - 1867-3880

VL - 7

SP - 2108

EP - 2112

JO - ChemCatChem

JF - ChemCatChem

IS - 14

ER -

Versatile relay and cooperative palladium(0) N-heterocyclic carbene/copper(I) N-heterocyclic carbene catalysis for the synthesis of tri- and tetrasubstituted alkenes

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Catalytic C-H bond functionalisation: Catalytic C-H bond functionalisation

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Versatile relay and cooperative palladium(0) N-heterocyclic carbene/copper(I) N-heterocyclic carbene catalysis for the synthesis of tri- and tetrasubstituted alkenes

Abstract

Keywords

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Catalytic C-H bond functionalisation: Catalytic C-H bond functionalisation

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