Zwitterion-Initiated Hydroboration of Alkynes and Styrene

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

doi:10.1002/adsc.202001323

Zwitterion-Initiated Hydroboration of Alkynes and Styrene

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

^*Corresponding author for this work

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

Abstract

The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C₆F₅)₃) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C₆F₅)₃) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C₆F₅)_3.

Original language	English
Article number	363
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Early online date	7 Jan 2021
DOIs	https://doi.org/10.1002/adsc.202001323
Publication status	E-pub ahead of print - 7 Jan 2021

Keywords / Materials (for Non-textual outputs)

alkyne
homogeneous catalysis
hydroboration
main-group chemistry
Zwitterion

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10.1002/adsc.202001323

20210302_Thomas_adsc.202001323Final published version, 3.51 MBLicence: Creative Commons: Attribution (CC-BY)

https://onlinelibrary.wiley.com/doi/full/10.1002/adsc.202001323

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@article{6f31464c7dce44a1acf2ca1371c65247,

title = "Zwitterion-Initiated Hydroboration of Alkynes and Styrene",

abstract = "The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C6F5)3) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C6F5)3) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3. ",

keywords = "alkyne, homogeneous catalysis, hydroboration, main-group chemistry, Zwitterion",

author = "Alessandro Bismuto and Cowley, {Michael J.} and Thomas, {Stephen P.}",

note = "Funding Information: SPT thanks the Royal Society for a University Research Fellowship (URF\R\191015). Both MJC and SPT thank the University of Edinburgh for funding. All thank the EPSRC and CRITICAT CDT for financial support (Ph.D. studentship to A.B.; EP/L016419/1). Publisher Copyright: {\textcopyright} 2021 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",

year = "2021",

month = jan,

day = "7",

doi = "10.1002/adsc.202001323",

language = "English",

journal = "Advanced Synthesis and Catalysis",

issn = "1615-4150",

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TY - JOUR

T1 - Zwitterion-Initiated Hydroboration of Alkynes and Styrene

AU - Bismuto, Alessandro

AU - Cowley, Michael J.

AU - Thomas, Stephen P.

N1 - Funding Information: SPT thanks the Royal Society for a University Research Fellowship (URF\R\191015). Both MJC and SPT thank the University of Edinburgh for funding. All thank the EPSRC and CRITICAT CDT for financial support (Ph.D. studentship to A.B.; EP/L016419/1). Publisher Copyright: © 2021 The Authors. Advanced Synthesis & Catalysis published by Wiley-VCH GmbH Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/1/7

Y1 - 2021/1/7

N2 - The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C6F5)3) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C6F5)3) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3.

AB - The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C6F5)3) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C6F5)3) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane-catalysed hydroboration and 1,1-carboboration of alkynes with B(C6F5)3.

KW - alkyne

KW - homogeneous catalysis

KW - hydroboration

KW - main-group chemistry

KW - Zwitterion

U2 - 10.1002/adsc.202001323

DO - 10.1002/adsc.202001323

M3 - Article

AN - SCOPUS:85099185481

SN - 1615-4150

JO - Advanced Synthesis and Catalysis

JF - Advanced Synthesis and Catalysis

M1 - 363

ER -

Zwitterion-Initiated Hydroboration of Alkynes and Styrene

Abstract

Keywords / Materials (for Non-textual outputs)

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