Carbon monoxide-promoted carbene insertion into the aryl substituent of an N-heterocyclic carbene ligand: Buchner reaction in a ruthenium carbene complex

In the presence of carbon monoxide, ruthenium carbenes give a net insertion/ring expansion (Buchner reaction) into one of the aromatic rings of the N-heterocyclic carbene ligand. In alkene metathesis applications, the N-heterocyclic carbene ligand is both robust and typically inert to reactions with the metal-bound carbene. This unique reaction is completely regioselective. The complexes obtained through ring expansion were fully characterized in the solid state using X-ray crystallography and in solution using NMR and IR spectroscopy. Copyright © 2005 American Chemical Society.