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Decarboxylative Allylation of Amino Alkanoic Acids and Esters via Dual Catalysis
[Image: see text] A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant α-amino and phenylacetic allyl esters. This operationally simple process produces CO(2) as the only byproduct and provides direct acce...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society
2014
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183636/ https://www.ncbi.nlm.nih.gov/pubmed/25228064 http://dx.doi.org/10.1021/ja508317j |
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author | Lang, Simon B. O’Nele, Kathryn M. Tunge, Jon A. |
author_facet | Lang, Simon B. O’Nele, Kathryn M. Tunge, Jon A. |
author_sort | Lang, Simon B. |
collection | PubMed |
description | [Image: see text] A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant α-amino and phenylacetic allyl esters. This operationally simple process produces CO(2) as the only byproduct and provides direct access to allylated alkanes. After photochemical oxidation, the carboxylate undergoes radical decarboxylation to site-specifically generate radical intermediates which undergo allylation. A radical dual catalysis mechanism is proposed. Free phenylacetic acids were also allylated utilizing similar reactions conditions. |
format | Online Article Text |
id | pubmed-4183636 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | American Chemical
Society |
record_format | MEDLINE/PubMed |
spelling | pubmed-41836362015-09-17 Decarboxylative Allylation of Amino Alkanoic Acids and Esters via Dual Catalysis Lang, Simon B. O’Nele, Kathryn M. Tunge, Jon A. J Am Chem Soc [Image: see text] A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant α-amino and phenylacetic allyl esters. This operationally simple process produces CO(2) as the only byproduct and provides direct access to allylated alkanes. After photochemical oxidation, the carboxylate undergoes radical decarboxylation to site-specifically generate radical intermediates which undergo allylation. A radical dual catalysis mechanism is proposed. Free phenylacetic acids were also allylated utilizing similar reactions conditions. American Chemical Society 2014-09-17 2014-10-01 /pmc/articles/PMC4183636/ /pubmed/25228064 http://dx.doi.org/10.1021/ja508317j Text en Copyright © 2014 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) |
spellingShingle | Lang, Simon B. O’Nele, Kathryn M. Tunge, Jon A. Decarboxylative Allylation of Amino Alkanoic Acids and Esters via Dual Catalysis |
title | Decarboxylative
Allylation of Amino Alkanoic Acids
and Esters via Dual Catalysis |
title_full | Decarboxylative
Allylation of Amino Alkanoic Acids
and Esters via Dual Catalysis |
title_fullStr | Decarboxylative
Allylation of Amino Alkanoic Acids
and Esters via Dual Catalysis |
title_full_unstemmed | Decarboxylative
Allylation of Amino Alkanoic Acids
and Esters via Dual Catalysis |
title_short | Decarboxylative
Allylation of Amino Alkanoic Acids
and Esters via Dual Catalysis |
title_sort | decarboxylative
allylation of amino alkanoic acids
and esters via dual catalysis |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4183636/ https://www.ncbi.nlm.nih.gov/pubmed/25228064 http://dx.doi.org/10.1021/ja508317j |
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