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...

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Autores principales: Lang, Simon B., O’Nele, Kathryn M., Tunge, Jon A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
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.
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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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AT tungejona decarboxylativeallylationofaminoalkanoicacidsandestersviadualcatalysis

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