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Spectroscopic and Structural Characterization of the CyNHC Adduct of B2pin2 in Solution and in the Solid State

Author:
Kleeberg, Christian, Crawford, Andrew G., Batsanov, Andrei S., Hodgkinson, Paul, Apperley, David C., Cheung, Man Sing, Lin, Zhenyang, Marder, Todd B.
Source:
Journal of organic chemistry 2012 v.77 no.1 pp. 785-789
ISSN:
1520-6904
Subject:
Lewis bases, boron, chemical reactions, dissociation, ketones, moieties, nuclear magnetic resonance spectroscopy, organic chemistry
Abstract:
The Lewis base adduct of B₂pin₂ 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.
Agid:
5498680