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Issue 29, 2016
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Synthesis and characterisation of an N-heterocyclic carbene with spatially-defined steric impact

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Abstract

The synthesis and co-ordination chemistry of a new ‘bulky yet flexible’ N-heterocyclic carbene (“IPaul”) is reported. This carbene has spatially-defined steric impact; steric maps show that two quadrants are very bulky while the other two are quite open. The electronic properties of this carbene are very similar to those of other 1,3-diarylimidazol-2-ylidenes. Copper, silver, iridium, and nickel complexes of the new ligand have been prepared. In solution, the ligand adopts two different conformations, while X-ray crystallographic analyses of the transition metal complexes suggest that the syn-conformer is preferred in the solid state due to intermolecular interactions. The copper(I) chloride complex of this new ligand has been shown to be highly-active in the hydrosilylation of carbonyl compounds, when compared to the analogous IPr, IMes, IPr* and IPr*OMe complexes.

Graphical abstract: Synthesis and characterisation of an N-heterocyclic carbene with spatially-defined steric impact

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Supplementary files

Article information


Submitted
25 May 2016
Accepted
15 Jun 2016
First published
16 Jun 2016

Dalton Trans., 2016,45, 11772-11780
Article type
Paper
Author version available

Synthesis and characterisation of an N-heterocyclic carbene with spatially-defined steric impact

P. Shaw, A. R. Kennedy and D. J. Nelson, Dalton Trans., 2016, 45, 11772
DOI: 10.1039/C6DT02100J

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