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

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Bidal_2015_ASC_Copper_I_AM.pdf (886.4Kb)
Date
12/10/2015
Author
Bidal, Yannick Daniel
Lesieur, Mathieu
Melaimi, Mohand
Nahra, Fady
Cordes, David Bradford
Athukorala Arachchige, Kasun Sankalpa
Slawin, Alexandra Martha Zoya
Bertrand, Guy
Cazin, Catherine S.J.
Keywords
Copper
Abnormal carbene
Remote carbene
N-heterocyclic carbene
Click chemistry
[3+2] cycloaddition
QD Chemistry
NDAS
Metadata
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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.
Citation
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 , vol. 357 , no. 14-15 , pp. 3155–3161 . https://doi.org/10.1002/adsc.201500453
Publication
Advanced Synthesis & Catalysis
Status
Peer reviewed
DOI
https://doi.org/10.1002/adsc.201500453
ISSN
1615-4150
Type
Journal article
Rights
© 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
Description
The authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC) and the DOE (DE-FG02-13ER16370) for financial support.
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  • University of St Andrews Research
URL
http://onlinelibrary.wiley.com/doi/10.1002/adsc.201500453/suppinfo
URI
http://hdl.handle.net/10023/9653

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