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Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin
Andrew D Bage1, Thomas A Hunt2, Stephen P Thomas1
1EaStCHEM School of Chemistry, University of Edinburgh, David Brewster Road, Edinburgh EH9 3FJ, United Kingdom.
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 NaOBu, Na[N(SiMe3)2], Bu2Mg, and BuLi only promoted the formation of BH3 and were not "true" hydroboration catalysts.
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