Spectroscopic and Structural Characterization of the CyNHC Adduct of B2pin2 in Solution and in the Solid State
The Journal of Organic Chemistry2011Vol. 77(1), pp. 785–789
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Christian Kleeberg, A.G. Crawford, Andrei S. Batsanov, Paul Hodgkinson, David C. Apperley, Man Sing Cheung, Zhenyang Lin, Todd B. Marder
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.
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