Aluminum Hydride Catalyzed Hydroboration of Alkynes

Alessandro Bismuto; Stephen P. Thomas; Michael J. Cowley

doi:10.1002/anie.201609690

Aluminum Hydride Catalyzed Hydroboration of Alkynes

Alessandro Bismuto, Stephen P. Thomas, Michael J. Cowley

Research output: Contribution to journal › Article › peer-review

Abstract

An aluminum-catalyzed hydroboration of alkynes using either the commercially available aluminum hydride DIBAL-H or bench-stable Et3Al⋅DABCO as the catalyst and H-Bpin as both the boron reagent and stoichiometric hydride source has been developed. Mechanistic studies revealed a unique mode of reactivity in which the reaction is proposed to proceed through hydroalumination and σ-bond metathesis between the resultant alkenyl aluminum species and HBpin, which acts to drive turnover of the catalytic cycle.

Original language	English
Pages (from-to)	15356-15359
Number of pages	4
Journal	Angewandte Chemie International Edition
Volume	55
Issue number	49
Early online date	11 Nov 2016
DOIs	https://doi.org/10.1002/anie.201609690
Publication status	Published - 5 Dec 2016

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10.1002/anie.201609690

20161024 Cowley aluminum-hydride catalyzed hydroboration of alkynesAccepted author manuscript, 240 KB

http://doi.wiley.com/10.1002/anie.201609690

Michael Cowley
- School of Chemistry - Senior Lecturer
- EaStCHEM
Person: Academic: Research Active

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abstract = "An aluminum-catalyzed hydroboration of alkynes using either the commercially available aluminum hydride DIBAL-H or bench-stable Et3Al⋅DABCO as the catalyst and H-Bpin as both the boron reagent and stoichiometric hydride source has been developed. Mechanistic studies revealed a unique mode of reactivity in which the reaction is proposed to proceed through hydroalumination and σ-bond metathesis between the resultant alkenyl aluminum species and HBpin, which acts to drive turnover of the catalytic cycle.",

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AB - An aluminum-catalyzed hydroboration of alkynes using either the commercially available aluminum hydride DIBAL-H or bench-stable Et3Al⋅DABCO as the catalyst and H-Bpin as both the boron reagent and stoichiometric hydride source has been developed. Mechanistic studies revealed a unique mode of reactivity in which the reaction is proposed to proceed through hydroalumination and σ-bond metathesis between the resultant alkenyl aluminum species and HBpin, which acts to drive turnover of the catalytic cycle.

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Aluminum Hydride Catalyzed Hydroboration of Alkynes

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