Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin

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

doi:10.1021/acs.orglett.0c01168

Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin

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

Research output: Contribution to journal › Article › peer-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 language	English
Journal	Organic letters
Early online date	7 May 2020
DOIs	https://doi.org/10.1021/acs.orglett.0c01168
Publication status	E-pub ahead of print - 7 May 2020

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https://pubs.acs.org/doi/10.1021/acs.orglett.0c01168

Stephen Thomas
- School of Chemistry - Personal Chair of Sustainable Catalysis
- EaStCHEM
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title = "Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin",

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.",

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journal = "Organic letters",

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N2 - 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.

AB - 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.

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M3 - Article

SN - 1523-7060

JO - Organic letters

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Hidden Boron Catalysis: Nucleophile-Promoted Decomposition of HBpin

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Stephen Thomas

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