Copper(I) complexes bearing carbenes beyond classical N-heterocyclic carbenes : synthesis and catalytic activity in “click chemistry”
MetadataShow full item record
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.
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
Advanced Synthesis & Catalysis
© 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
DescriptionThe authors gratefully acknowledge the Royal Society (University Research Fellowship to CSJC) and the DOE (DE-FG02-13ER16370) for financial support.
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.
Showing items related by title, author, creator and subject.
Investigating the structure and reactivity of azolyl-based copper(I)-NHC complexes : the role of the anionic ligand Trose, Michael; Nahra, Fady; Poater, Albert; Cordes, David B.; Slawin, Alexandra M. Z.; Cavallo, Luigi; Cazin, Catherine S. J. (2017-12) - Journal articleA family of copper(I)-NHC azolyl complexes was synthesized and deployed in the hydrosilylation of dicyclo-hexylketone to probe the role of the anionic ligand on catalytic performance. The azolyl ligand is shown to have a ...
Mechanistic insights into the triazolylidene-catalysed Stetter and benzoin reactions : role of the N-aryl substituent Collett, Christopher J.; Massey, Richard S.; Maguire, Oliver R.; Batsanov, Andrei S.; O'Donoghue, AnnMarie C.; Smith, Andrew D. (2013) - Journal articleThe in situ observation, isolation and reversible formation of intermediate 3-(hydroxybenzyl) azolium salts derived from NHC addition to a range of substituted benzaldehydes is probed. Equilibrium constants for the formation ...
Generalization of the copper to late-transition-metal transmetallation to carbenes beyond N-heterocyclic carbenes Bidal, Yannick D.; Santoro, Orlando; Melaimi, Mohand; Cordes, David B.; Slawin, Alexandra M. Z.; Bertrand, Guy; Cazin, Catherine S. J. (2016-06-23) - Journal articleCarbene transition-metal complexes have become a prevalent family of catalysts enabling numerous organic transformations. Their facile synthetic access is a matter of great importance. To this end, the CuI-NHC transfer ...