Issue 20, 2013

Electronic bond tuning with heterocyclic carbenes

Abstract

We discuss the impact of the nature of the heterocyclic carbene ring, when used as a complex forming ligand, on the relative stability of key intermediates in three typical Ru, Pd and Au promoted reactions. Results show that P-heterocyclic carbenes have a propensity to increase the bonding of the labile ligand and of the substrate in Ru-promoted olefin metathesis, whereas negligible impact is expected on the stability of the ruthenacycle intermediate. In the case of Pd cross-coupling reactions, dissociation of a P-heterocyclic carbene is easier than dissociation of the N-heterocyclic analogue. In the case of the Au–OH synthon, the Au–OH bond is weakened with the P-heterocyclic carbene ligands. A detailed energy decomposition analysis is performed to rationalize these results.

Graphical abstract: Electronic bond tuning with heterocyclic carbenes

Supplementary files

Article information

Article type
Paper
Submitted
05 Dec 2012
Accepted
10 Jan 2013
First published
29 Jan 2013

Dalton Trans., 2013,42, 7281-7286

Electronic bond tuning with heterocyclic carbenes

L. Falivene, L. Caporaso, L. Cavallo and H. Jacobsen, Dalton Trans., 2013, 42, 7281 DOI: 10.1039/C3DT32923B

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