Spectroscopic and structural characterization of the CyNHC adduct of B2pin2 in solution and in the solid state

J Org Chem. 2012 Jan 6;77(1):785-9. doi: 10.1021/jo202127c. Epub 2011 Dec 12.

Abstract

The Lewis base adduct of B(2)pin(2) and the NHC (1,3-bis(cyclohexyl)imidazol-2-ylidene), which was proposed to act as a source of nucleophilic boryl groups in the β-borylation of α,β-unsaturated ketones, has been isolated, and its solid state structure and solution behavior was studied. In solution, the binding is weak, and NMR spectroscopy reveals a rapid exchange of the NHC between the two boron centers. DFT calculations reveal that the exchange involves dissociation and reassociation of NHC rather than an intramolecular process.