Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes: synthesis and catalytic activity in “click chemistry”

Yannick Daniel Bidal; Mathieu Lesieur; Mohand  Melaimi; Fady Nahra; David Bradford Cordes; Kasun Sankalpa Athukorala Arachchige; Alexandra Martha Zoya Slawin; Guy  Bertrand; Catherine S.J. Cazin

doi:10.1002/adsc.201500453

Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes: synthesis and catalytic activity in “click chemistry”

Yannick Daniel Bidal, Mathieu Lesieur, Mohand Melaimi, Fady Nahra, David Bradford Cordes, Kasun Sankalpa Athukorala Arachchige, Alexandra Martha Zoya Slawin, Guy Bertrand, Catherine S.J. Cazin

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

Abstract

The synthesis and characterization of abnormal N-heterocyclic carbene, cyclic (alkyl)(amino)carbene, and mesoionic carbene copper(I) complexes are reported. These organometallic species are obtained via a versatile and inexpensive synthetic pathway using readily available reactants, namely copper oxide and iminium salts. The catalytic activity of this series of complexes was evaluated in the [3+2] cycloaddition of alkynes with azides (CuAAC). Outstanding catalytic properties were
observed for the abnormal NHC- and triazolylidene-based copper(I) complexes.

Original language	English
Pages (from-to)	3155–3161
Journal	Advanced Synthesis & Catalysis
Volume	357
Issue number	14-15
DOIs	https://doi.org/10.1002/adsc.201500453
Publication status	Published - 12 Oct 2015

Keywords

Copper
Abnormal carbene
Remote carbene
N-heterocyclic carbene
Click chemistry
[3+2] cycloaddition

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10.1002/adsc.201500453

Bidal_2015_ASC_Copper(I)_AM
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. This work is 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://dx.doi.org/10.1002/adsc.201500453
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Bidal, Y. D., Lesieur, M., Melaimi, M., Nahra, F., Cordes, D. B., Athukorala Arachchige, K. S., Slawin, A. M. Z., Bertrand, G., & Cazin, C. S. J. (2015). Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes: synthesis and catalytic activity in “click chemistry”. Advanced Synthesis & Catalysis, 357(14-15), 3155–3161. https://doi.org/10.1002/adsc.201500453

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title = "Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes: synthesis and catalytic activity in “click chemistry”",

abstract = "The synthesis and characterization of abnormal N-heterocyclic carbene, cyclic (alkyl)(amino)carbene, and mesoionic carbene copper(I) complexes are reported. These organometallic species are obtained via a versatile and inexpensive synthetic pathway using readily available reactants, namely copper oxide and iminium salts. The catalytic activity of this series of complexes was evaluated in the [3+2] cycloaddition of alkynes with azides (CuAAC). Outstanding catalytic properties were observed for the abnormal NHC- and triazolylidene-based copper(I) complexes.",

keywords = "Copper, Abnormal carbene, Remote carbene, N-heterocyclic carbene, Click chemistry, [3+2] cycloaddition",

author = "Bidal, {Yannick Daniel} and Mathieu Lesieur and Mohand Melaimi and Fady Nahra and Cordes, {David Bradford} and {Athukorala Arachchige}, {Kasun Sankalpa} and Slawin, {Alexandra Martha Zoya} and Guy Bertrand and Cazin, {Catherine S.J.}",

note = "The authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC) and the DOE (DE-FG02-13ER16370) for financial support. ",

year = "2015",

month = oct,

day = "12",

doi = "10.1002/adsc.201500453",

language = "English",

volume = "357",

pages = "3155–3161",

journal = "Advanced Synthesis & Catalysis",

issn = "1615-4150",

publisher = "John Wiley & Sons, Ltd",

number = "14-15",

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Bidal, YD, Lesieur, M, Melaimi, M, Nahra, F, Cordes, DB, Athukorala Arachchige, KS, Slawin, AMZ, Bertrand, G & Cazin, CSJ 2015, 'Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes: synthesis and catalytic activity in “click chemistry”', Advanced Synthesis & Catalysis, vol. 357, no. 14-15, pp. 3155–3161. https://doi.org/10.1002/adsc.201500453

TY - JOUR

T1 - Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes

T2 - synthesis and catalytic activity in “click chemistry”

AU - Bidal, Yannick Daniel

AU - Lesieur, Mathieu

AU - Melaimi, Mohand

AU - Nahra, Fady

AU - Cordes, David Bradford

AU - Athukorala Arachchige, Kasun Sankalpa

AU - Slawin, Alexandra Martha Zoya

AU - Bertrand, Guy

AU - Cazin, Catherine S.J.

N1 - The authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC) and the DOE (DE-FG02-13ER16370) for financial support.

PY - 2015/10/12

Y1 - 2015/10/12

N2 - The synthesis and characterization of abnormal N-heterocyclic carbene, cyclic (alkyl)(amino)carbene, and mesoionic carbene copper(I) complexes are reported. These organometallic species are obtained via a versatile and inexpensive synthetic pathway using readily available reactants, namely copper oxide and iminium salts. The catalytic activity of this series of complexes was evaluated in the [3+2] cycloaddition of alkynes with azides (CuAAC). Outstanding catalytic properties were observed for the abnormal NHC- and triazolylidene-based copper(I) complexes.

AB - The synthesis and characterization of abnormal N-heterocyclic carbene, cyclic (alkyl)(amino)carbene, and mesoionic carbene copper(I) complexes are reported. These organometallic species are obtained via a versatile and inexpensive synthetic pathway using readily available reactants, namely copper oxide and iminium salts. The catalytic activity of this series of complexes was evaluated in the [3+2] cycloaddition of alkynes with azides (CuAAC). Outstanding catalytic properties were observed for the abnormal NHC- and triazolylidene-based copper(I) complexes.

KW - Copper

KW - Abnormal carbene

KW - Remote carbene

KW - N-heterocyclic carbene

KW - Click chemistry

KW - [3+2] cycloaddition

UR - http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500453/suppinfo

U2 - 10.1002/adsc.201500453

DO - 10.1002/adsc.201500453

M3 - Article

SN - 1615-4150

VL - 357

SP - 3155

EP - 3161

JO - Advanced Synthesis & Catalysis

JF - Advanced Synthesis & Catalysis

IS - 14-15

ER -

Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes: synthesis and catalytic activity in “click chemistry”

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Keywords

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Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

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

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Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes: synthesis and catalytic activity in “click chemistry”

Abstract

Keywords

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Structuring the Future: Structuring the Future - Underpinning world-leading science in EaStCHEM through cutting edge characterisation

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

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