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

Chemistry

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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A Boron-Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes. / Docherty, Jamie H.; Nicholson, Kieran; Dominey, Andrew P. et al.
In: ACS Catalysis, Vol. 10, No. 8, 17.04.2020, p. 4686-4691.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

Docherty, JH, Nicholson, K, Dominey, AP & Thomas, SP 2020, 'A Boron-Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes', ACS Catalysis, vol. 10, no. 8, pp. 4686-4691. https://doi.org/10.1021/acscatal.0c00869

APA

Docherty, J. H., Nicholson, K., Dominey, A. P., & Thomas, S. P. (2020). A Boron-Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes. ACS Catalysis, 10(8), 4686-4691. https://doi.org/10.1021/acscatal.0c00869

Vancouver

Docherty JH, Nicholson K, Dominey AP, Thomas SP. A Boron-Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes. ACS Catalysis. 2020 Apr 17;10(8):4686-4691. doi: 10.1021/acscatal.0c00869

Author

Docherty, Jamie H. ; Nicholson, Kieran ; Dominey, Andrew P. et al. / A Boron-Boron Double Transborylation Strategy for the Synthesis of gem-Diborylalkanes. In: ACS Catalysis. 2020 ; Vol. 10, No. 8. pp. 4686-4691.

Bibtex

@article{4a8d7423bb6143819f5b8508fdbbc39b,

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.",

keywords = "bond-metathesis, borane, boron, diboryl, hydroboration",

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

year = "2020",

month = apr,

day = "17",

doi = "10.1021/acscatal.0c00869",

language = "English",

volume = "10",

pages = "4686--4691",

journal = "ACS Catalysis",

issn = "2155-5435",

publisher = "American Chemical Society",

number = "8",

}

RIS

TY - JOUR

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 - 2020/4/17

Y1 - 2020/4/17

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.

KW - bond-metathesis

KW - borane

KW - boron

KW - diboryl

KW - hydroboration

UR - http://www.scopus.com/inward/record.url?scp=85083293513&partnerID=8YFLogxK

U2 - 10.1021/acscatal.0c00869

DO - 10.1021/acscatal.0c00869

M3 - Journal article

AN - SCOPUS:85083293513

VL - 10

SP - 4686

EP - 4691

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 8

ER -

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