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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical Society
2023
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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. |
format | Online Article Text |
id | pubmed-10032571 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT stantonmichaelp coppercatalyzeddecarboxylativeeliminationofcarboxylicacidstostyrenes AT hooverjessicam coppercatalyzeddecarboxylativeeliminationofcarboxylicacidstostyrenes |