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Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes

[Image: see text] 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 photocatalys...

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Autores principales: Stanton, Michael P., Hoover, Jessica M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10032571/
https://www.ncbi.nlm.nih.gov/pubmed/36662592
http://dx.doi.org/10.1021/acs.joc.2c02705
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author Stanton, Michael P.
Hoover, Jessica M.
author_facet Stanton, Michael P.
Hoover, Jessica M.
author_sort Stanton, Michael P.
collection PubMed
description [Image: see text] 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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spelling pubmed-100325712023-03-23 Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes Stanton, Michael P. Hoover, Jessica M. J Org Chem [Image: see text] 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. American Chemical Society 2023-01-20 /pmc/articles/PMC10032571/ /pubmed/36662592 http://dx.doi.org/10.1021/acs.joc.2c02705 Text en © 2023 American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Stanton, Michael P.
Hoover, Jessica M.
Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes
title Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes
title_full Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes
title_fullStr Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes
title_full_unstemmed Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes
title_short Copper-Catalyzed Decarboxylative Elimination of Carboxylic Acids to Styrenes
title_sort copper-catalyzed decarboxylative elimination of carboxylic acids to styrenes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10032571/
https://www.ncbi.nlm.nih.gov/pubmed/36662592
http://dx.doi.org/10.1021/acs.joc.2c02705
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