A Boron–Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes

Jamie H. Docherty; Kieran Nicholson; Andrew P. Dominey; Stephen P. Thomas

doi:10.1021/acscatal.0c00869

A Boron–Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes

Jamie H. Docherty, Kieran Nicholson, Andrew P. Dominey, Stephen P. Thomas

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Abstract / Description of output

Olefin hydroboration reactions provide efficient access to synthetically versatile and easily handled organoboronic esters. In this study, we demonstrate that the commercially available organoborane reagent 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) can serve as a catalyst for the sequential double hydroboration of alkynes using pinacolborane (HBpin). This strategy, which is effective for a wide range of terminal alkynes, is predicated upon a key C(sp3)−B/B–H transborylation reaction. Transition-state thermodynamic parameters and 10-boron-isotopic labeling experiments are indicative of a σ-bond metathesis exchange pathway.

Original language	English
Pages (from-to)	4686-4691
Journal	ACS Catalysis
Early online date	30 Mar 2020
DOIs	https://doi.org/10.1021/acscatal.0c00869
Publication status	E-pub ahead of print - 30 Mar 2020

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https://pubs.acs.org/doi/10.1021/acscatal.0c00869

Stephen Thomas
- School of Chemistry - Personal Chair of Sustainable Catalysis
- EaStCHEM
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title = "A Boron–Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes",

abstract = "Olefin hydroboration reactions provide efficient access to synthetically versatile and easily handled organoboronic esters. In this study, we demonstrate that the commercially available organoborane reagent 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) can serve as a catalyst for the sequential double hydroboration of alkynes using pinacolborane (HBpin). This strategy, which is effective for a wide range of terminal alkynes, is predicated upon a key C(sp3)−B/B–H transborylation reaction. Transition-state thermodynamic parameters and 10-boron-isotopic labeling experiments are indicative of a σ-bond metathesis exchange pathway.",

author = "Docherty, {Jamie H.} and Kieran Nicholson and Dominey, {Andrew P.} and Thomas, {Stephen P.}",

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doi = "10.1021/acscatal.0c00869",

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T1 - A Boron–Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes

AU - Docherty, Jamie H.

AU - Nicholson, Kieran

AU - Dominey, Andrew P.

AU - Thomas, Stephen P.

PY - 2020/3/30

Y1 - 2020/3/30

N2 - Olefin hydroboration reactions provide efficient access to synthetically versatile and easily handled organoboronic esters. In this study, we demonstrate that the commercially available organoborane reagent 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) can serve as a catalyst for the sequential double hydroboration of alkynes using pinacolborane (HBpin). This strategy, which is effective for a wide range of terminal alkynes, is predicated upon a key C(sp3)−B/B–H transborylation reaction. Transition-state thermodynamic parameters and 10-boron-isotopic labeling experiments are indicative of a σ-bond metathesis exchange pathway.

AB - Olefin hydroboration reactions provide efficient access to synthetically versatile and easily handled organoboronic esters. In this study, we demonstrate that the commercially available organoborane reagent 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) can serve as a catalyst for the sequential double hydroboration of alkynes using pinacolborane (HBpin). This strategy, which is effective for a wide range of terminal alkynes, is predicated upon a key C(sp3)−B/B–H transborylation reaction. Transition-state thermodynamic parameters and 10-boron-isotopic labeling experiments are indicative of a σ-bond metathesis exchange pathway.

U2 - 10.1021/acscatal.0c00869

DO - 10.1021/acscatal.0c00869

M3 - Article

SN - 2155-5435

SP - 4686

EP - 4691

JO - ACS Catalysis

JF - ACS Catalysis

ER -

A Boron–Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes

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Stephen Thomas

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