Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin

Andrew D. Bage, Thomas A. Hunt, Stephen P. Thomas

Research output: Contribution to journalArticlepeer-review

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.
Original languageEnglish
JournalOrganic letters
Early online date7 May 2020
DOIs
Publication statusE-pub ahead of print - 7 May 2020

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