Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin
Andrew D. Bage, Thomas A. Hunt, Stephen P. Thomas
Abstract
Simple nucleophiles with structural similarities to known hydroboration catalysts can readily mediate the formation of BH3 and borohydride species from pinacolborane (HBpin). Alkyne and alkene hydroboration reactions were successfully mediated by nucleophiles through BH3 generation, with BH3-catalyzed hydroboration found to dominate catalysis. NMR spectroscopy and kinetic analyses showed that the nucleophiles NaOtBu, Na[N(SiMe3)2], nBu2Mg, and nBuLi only promoted the formation of BH3 and were not “true” hydroboration catalysts.
Topics & Concepts
HydroborationChemistryNucleophileCatalysisAlkeneAlkyneBoronOrganic chemistryMedicinal chemistryPhotochemistryCombinatorial chemistryOrganoboron and organosilicon chemistryBoron Compounds in ChemistryBoron and Carbon Nanomaterials Research