B(C6F5)3-Catalyzed (E)-Selective Isomerization of Alkenes

Betty A Kustiana; Salma A Elsherbeni; Thomas G Linford-Wood; Rebecca L Melen; Matthew N Grayson; Louis Christian Morrill

doi:10.1002/chem.202202454

B(C6F5)3-Catalyzed (E)-Selective Isomerization of Alkenes

Betty A Kustiana, Salma A Elsherbeni, Thomas G Linford-Wood, Rebecca L Melen, Matthew N Grayson, Louis Christian Morrill

Department of Chemistry

Cardiff University

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

9 Citations (SciVal)

147 Downloads (Pure)

Abstract

Herein, we report the B(C ₆F ₅) ₃-catalyzed E-selective isomerization of alkenes. The transition-metal-free method is applicable across a diverse array of readily accessible substrates, giving access to a broad range of synthetically useful products containing versatile stereodefined internal alkenes. The reaction mechanism was investigated by using synthetic and computational methods.

Original language	English
Article number	e202202454
Journal	Chemistry - A European Journal
Volume	28
Issue number	63
Early online date	9 Aug 2022
DOIs	https://doi.org/10.1002/chem.202202454
Publication status	Published - 14 Nov 2022

Bibliographical note

Funding Information:
We gratefully acknowledge the School of Chemistry, Cardiff University for generous support, the Schlumberger Foundation for a Faculty for the Future Fellowship (B.A.K.), the British Council and the Egyptian Cultural Affairs and Missions Sector for a PhD studentship through the Newton‐Mosharafa Fund (S.A.E.). The EPSRC and the Centre for Doctoral Training in Catalysis (PhD studentship awarded to T.G.L.‐W., EP/L016443/1) are thanked for funding. Part of this work was completed by using the Balena HPC service at the University of Bath ( https://www.bath.ac.uk/corporateinformation/balena‐hpc‐cluster/ ).

Keywords

alkenes
borane catalysis
isomerization

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.202202454Licence: CC BY

Chemistry A European J - 2022 - Kustiana - B C6F5 3‐Catalyzed E‐Selective Isomerization of Alkenes (1)Final published version, 5.62 MBLicence: CC BY

Cite this

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title = "B(C6F5)3-Catalyzed (E)-Selective Isomerization of Alkenes",

abstract = "Herein, we report the B(C 6F 5) 3-catalyzed E-selective isomerization of alkenes. The transition-metal-free method is applicable across a diverse array of readily accessible substrates, giving access to a broad range of synthetically useful products containing versatile stereodefined internal alkenes. The reaction mechanism was investigated by using synthetic and computational methods. ",

keywords = "alkenes, borane catalysis, isomerization",

author = "Kustiana, {Betty A} and Elsherbeni, {Salma A} and Linford-Wood, {Thomas G} and Melen, {Rebecca L} and Grayson, {Matthew N} and Morrill, {Louis Christian}",

note = "Funding Information: We gratefully acknowledge the School of Chemistry, Cardiff University for generous support, the Schlumberger Foundation for a Faculty for the Future Fellowship (B.A.K.), the British Council and the Egyptian Cultural Affairs and Missions Sector for a PhD studentship through the Newton‐Mosharafa Fund (S.A.E.). The EPSRC and the Centre for Doctoral Training in Catalysis (PhD studentship awarded to T.G.L.‐W., EP/L016443/1) are thanked for funding. Part of this work was completed by using the Balena HPC service at the University of Bath ( https://www.bath.ac.uk/corporateinformation/balena‐hpc‐cluster/ ). ",

year = "2022",

month = nov,

day = "14",

doi = "10.1002/chem.202202454",

language = "English",

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journal = "Chemistry - A European Journal",

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TY - JOUR

T1 - B(C6F5)3-Catalyzed (E)-Selective Isomerization of Alkenes

AU - Kustiana, Betty A

AU - Elsherbeni, Salma A

AU - Linford-Wood, Thomas G

AU - Melen, Rebecca L

AU - Grayson, Matthew N

AU - Morrill, Louis Christian

N1 - Funding Information: We gratefully acknowledge the School of Chemistry, Cardiff University for generous support, the Schlumberger Foundation for a Faculty for the Future Fellowship (B.A.K.), the British Council and the Egyptian Cultural Affairs and Missions Sector for a PhD studentship through the Newton‐Mosharafa Fund (S.A.E.). The EPSRC and the Centre for Doctoral Training in Catalysis (PhD studentship awarded to T.G.L.‐W., EP/L016443/1) are thanked for funding. Part of this work was completed by using the Balena HPC service at the University of Bath ( https://www.bath.ac.uk/corporateinformation/balena‐hpc‐cluster/ ).

PY - 2022/11/14

Y1 - 2022/11/14

N2 - Herein, we report the B(C 6F 5) 3-catalyzed E-selective isomerization of alkenes. The transition-metal-free method is applicable across a diverse array of readily accessible substrates, giving access to a broad range of synthetically useful products containing versatile stereodefined internal alkenes. The reaction mechanism was investigated by using synthetic and computational methods.

AB - Herein, we report the B(C 6F 5) 3-catalyzed E-selective isomerization of alkenes. The transition-metal-free method is applicable across a diverse array of readily accessible substrates, giving access to a broad range of synthetically useful products containing versatile stereodefined internal alkenes. The reaction mechanism was investigated by using synthetic and computational methods.

KW - alkenes

KW - borane catalysis

KW - isomerization

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U2 - 10.1002/chem.202202454

DO - 10.1002/chem.202202454

M3 - Article

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VL - 28

JO - Chemistry - A European Journal

JF - Chemistry - A European Journal

IS - 63

M1 - e202202454

ER -

B(C6F5)3-Catalyzed (E)-Selective Isomerization of Alkenes

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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