Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins

Anas Alkayal; Volodymyr Tabas; Stephanie Montanaro; Iain A. Wright; Andrei V. Malkov; Benjamin R. Buckley

doi:10.1021/jacs.9b13305

Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins

Anas Alkayal, Volodymyr Tabas, Stephanie Montanaro, Iain A. Wright, Andrei V. Malkov^*, Benjamin R. Buckley

^*Corresponding author for this work

School of Chemistry

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

Abstract

The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.

Original language	English
Journal	Journal of the American Chemical Society
Early online date	21 Jan 2020
DOIs	https://doi.org/10.1021/jacs.9b13305
Publication status	E-pub ahead of print - 21 Jan 2020

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title = "Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins",

abstract = "The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.",

author = "Anas Alkayal and Volodymyr Tabas and Stephanie Montanaro and Wright, {Iain A.} and Malkov, {Andrei V.} and Buckley, {Benjamin R.}",

note = "Funding Information: We thank Loughborough University for PhD studentships (to V.T. and S.M.) and CARA for a Post-Doctoral Fellowship (to A.A.). We would also like to thank the EPSRC CO2Chem Grand Challenge Network for travel grants (to B.R.B. and V.T.) for dissemination of this work. Publisher Copyright: Copyright {\textcopyright} 2020 American Chemical Society.",

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doi = "10.1021/jacs.9b13305",

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journal = "Journal of the American Chemical Society",

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AU - Alkayal, Anas

AU - Tabas, Volodymyr

AU - Montanaro, Stephanie

AU - Wright, Iain A.

AU - Malkov, Andrei V.

AU - Buckley, Benjamin R.

N1 - Funding Information: We thank Loughborough University for PhD studentships (to V.T. and S.M.) and CARA for a Post-Doctoral Fellowship (to A.A.). We would also like to thank the EPSRC CO2Chem Grand Challenge Network for travel grants (to B.R.B. and V.T.) for dissemination of this work. Publisher Copyright: Copyright © 2020 American Chemical Society.

PY - 2020/1/21

Y1 - 2020/1/21

N2 - The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.

AB - The construction of carboxylic acid compounds in a selective fashion from low value materials such as alkenes remains a long-standing challenge to synthetic chemists. In particular, β-addition to styrenes is underdeveloped. Herein we report a new electrosynthetic approach to the selective hydrocarboxylation of alkenes that overcomes the limitations of current transition metal and photochemical approaches. The reported method allows unprecedented direct access to carboxylic acids derived from β,β-trisubstituted alkenes, in a highly regioselective manner.

U2 - 10.1021/jacs.9b13305

DO - 10.1021/jacs.9b13305

M3 - Article

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AN - SCOPUS:85078687416

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

ER -

Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins

Abstract

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