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A boron-oxygen transborylation strategy for a catalytic midland reduction

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

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A boron-oxygen transborylation strategy for a catalytic midland reduction. / Nicholson, Kieran; Dunne, Joanne; DaBell, Peter et al.
In: ACS Catalysis, Vol. 11, No. 4, 19.02.2021, p. 2034-2040.

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

Harvard

Nicholson, K, Dunne, J, DaBell, P, Garcia, AB, Bage, AD, Docherty, JH, Hunt, TA, Langer, T & Thomas, SP 2021, 'A boron-oxygen transborylation strategy for a catalytic midland reduction', ACS Catalysis, vol. 11, no. 4, pp. 2034-2040. https://doi.org/10.1021/acscatal.0c05168

APA

Nicholson, K., Dunne, J., DaBell, P., Garcia, A. B., Bage, A. D., Docherty, J. H., Hunt, T. A., Langer, T., & Thomas, S. P. (2021). A boron-oxygen transborylation strategy for a catalytic midland reduction. ACS Catalysis, 11(4), 2034-2040. https://doi.org/10.1021/acscatal.0c05168

Vancouver

Nicholson K, Dunne J, DaBell P, Garcia AB, Bage AD, Docherty JH et al. A boron-oxygen transborylation strategy for a catalytic midland reduction. ACS Catalysis. 2021 Feb 19;11(4):2034-2040. Epub 2021 Feb 1. doi: 10.1021/acscatal.0c05168

Author

Nicholson, Kieran ; Dunne, Joanne ; DaBell, Peter et al. / A boron-oxygen transborylation strategy for a catalytic midland reduction. In: ACS Catalysis. 2021 ; Vol. 11, No. 4. pp. 2034-2040.

Bibtex

@article{da5029a9ff26436d8f700302076d1efa,
title = "A boron-oxygen transborylation strategy for a catalytic midland reduction",
abstract = "The enantioselective hydroboration of ketones is a textbook reaction requiring stoichiometric amounts of an enantioenriched borane, with the Midland reduction being a seminal example. Here, a turnover strategy for asymmetric catalysis, boron.oxygen transborylation, has been developed and used to transform the stoichiometric borane reagents of the Midland reduction into catalysts. This turnover strategy was demonstrated by the enantioselective reduction of ketones, including derivatives of biologically active molecules and those containing reducible groups. The enantioenriched borane catalyst was generated in situ from commercially available reagents, 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) and β-pinene, and B.O transborylation with pinacolborane (HBpin) was used for catalytic turnover. Mechanistic studies indicated that B.O transborylation proceeded by B.O/B.H boron exchange through a stereoretentive, concerted transition state, resembling σ-bond metathesis.",
keywords = "Asymmetric catalysis, Boron, Enantioselective, Hydroboration, Ketone, Main group, Reduction, Transborylation",
author = "Kieran Nicholson and Joanne Dunne and Peter DaBell and Garcia, {Alexander Beaton} and Bage, {Andrew D.} and Docherty, {Jamie H.} and Hunt, {Thomas A.} and Thomas Langer and Thomas, {Stephen P.}",
year = "2021",
month = feb,
day = "19",
doi = "10.1021/acscatal.0c05168",
language = "English",
volume = "11",
pages = "2034--2040",
journal = "ACS Catalysis",
issn = "2155-5435",
publisher = "American Chemical Society",
number = "4",

}

RIS

TY - JOUR

T1 - A boron-oxygen transborylation strategy for a catalytic midland reduction

AU - Nicholson, Kieran

AU - Dunne, Joanne

AU - DaBell, Peter

AU - Garcia, Alexander Beaton

AU - Bage, Andrew D.

AU - Docherty, Jamie H.

AU - Hunt, Thomas A.

AU - Langer, Thomas

AU - Thomas, Stephen P.

PY - 2021/2/19

Y1 - 2021/2/19

N2 - The enantioselective hydroboration of ketones is a textbook reaction requiring stoichiometric amounts of an enantioenriched borane, with the Midland reduction being a seminal example. Here, a turnover strategy for asymmetric catalysis, boron.oxygen transborylation, has been developed and used to transform the stoichiometric borane reagents of the Midland reduction into catalysts. This turnover strategy was demonstrated by the enantioselective reduction of ketones, including derivatives of biologically active molecules and those containing reducible groups. The enantioenriched borane catalyst was generated in situ from commercially available reagents, 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) and β-pinene, and B.O transborylation with pinacolborane (HBpin) was used for catalytic turnover. Mechanistic studies indicated that B.O transborylation proceeded by B.O/B.H boron exchange through a stereoretentive, concerted transition state, resembling σ-bond metathesis.

AB - The enantioselective hydroboration of ketones is a textbook reaction requiring stoichiometric amounts of an enantioenriched borane, with the Midland reduction being a seminal example. Here, a turnover strategy for asymmetric catalysis, boron.oxygen transborylation, has been developed and used to transform the stoichiometric borane reagents of the Midland reduction into catalysts. This turnover strategy was demonstrated by the enantioselective reduction of ketones, including derivatives of biologically active molecules and those containing reducible groups. The enantioenriched borane catalyst was generated in situ from commercially available reagents, 9-borabicyclo[3.3.1]nonane (H-B-9-BBN) and β-pinene, and B.O transborylation with pinacolborane (HBpin) was used for catalytic turnover. Mechanistic studies indicated that B.O transborylation proceeded by B.O/B.H boron exchange through a stereoretentive, concerted transition state, resembling σ-bond metathesis.

KW - Asymmetric catalysis

KW - Boron

KW - Enantioselective

KW - Hydroboration

KW - Ketone

KW - Main group

KW - Reduction

KW - Transborylation

U2 - 10.1021/acscatal.0c05168

DO - 10.1021/acscatal.0c05168

M3 - Journal article

AN - SCOPUS:85100956309

VL - 11

SP - 2034

EP - 2040

JO - ACS Catalysis

JF - ACS Catalysis

SN - 2155-5435

IS - 4

ER -