Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes

Michael P. Stanton; Jessica M. Hoover

doi:10.1021/acs.joc.2c02705

Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes

Michael P. Stanton, Jessica M. Hoover

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

3 Scopus citations

Abstract

A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method furnishes alkenes from carboxylic acids without the need for stochiometric Pb or Ag additives or expensive or specialized photocatalysts. A series of mechanistic experiments indicate that the reaction proceeds via benzylic deprotonation and subsequent radical decarboxylation; a pathway that is distinct from the single-electron-transfer mechanisms implicated in related decarboxylative elimination reactions.

Original language	English (US)
Pages (from-to)	1713-1719
Number of pages	7
Journal	Journal of Organic Chemistry
Volume	88
Issue number	3
DOIs	https://doi.org/10.1021/acs.joc.2c02705
State	Published - Feb 3 2023
Externally published	Yes

Bibliographical note

Funding Information:
We are grateful to West Virginia University and the NSF (CHE-2102538) for financial support of this work. NMR spectroscopy facilities were partially supported by the NSF (CHE-1228336).

Publisher Copyright:
© 2023 American Chemical Society.

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abstract = "A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method furnishes alkenes from carboxylic acids without the need for stochiometric Pb or Ag additives or expensive or specialized photocatalysts. A series of mechanistic experiments indicate that the reaction proceeds via benzylic deprotonation and subsequent radical decarboxylation; a pathway that is distinct from the single-electron-transfer mechanisms implicated in related decarboxylative elimination reactions.",

author = "Stanton, {Michael P.} and Hoover, {Jessica M.}",

note = "Funding Information: We are grateful to West Virginia University and the NSF (CHE-2102538) for financial support of this work. NMR spectroscopy facilities were partially supported by the NSF (CHE-1228336). Publisher Copyright: {\textcopyright} 2023 American Chemical Society.",

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doi = "10.1021/acs.joc.2c02705",

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AU - Stanton, Michael P.

AU - Hoover, Jessica M.

N1 - Funding Information: We are grateful to West Virginia University and the NSF (CHE-2102538) for financial support of this work. NMR spectroscopy facilities were partially supported by the NSF (CHE-1228336). Publisher Copyright: © 2023 American Chemical Society.

PY - 2023/2/3

Y1 - 2023/2/3

N2 - A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method furnishes alkenes from carboxylic acids without the need for stochiometric Pb or Ag additives or expensive or specialized photocatalysts. A series of mechanistic experiments indicate that the reaction proceeds via benzylic deprotonation and subsequent radical decarboxylation; a pathway that is distinct from the single-electron-transfer mechanisms implicated in related decarboxylative elimination reactions.

AB - A copper-catalyzed decarboxylative elimination reaction of (hetero)aromatic propionic acids to vinyl (hetero)arenes has been developed. This method furnishes alkenes from carboxylic acids without the need for stochiometric Pb or Ag additives or expensive or specialized photocatalysts. A series of mechanistic experiments indicate that the reaction proceeds via benzylic deprotonation and subsequent radical decarboxylation; a pathway that is distinct from the single-electron-transfer mechanisms implicated in related decarboxylative elimination reactions.

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Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes

Abstract

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