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Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates

[Image: see text] Herein, we report a strategy for the formation of isotopically labeled carboxylic esters from boronic esters/acids using a readily accessible palladium carboxylate complex as an organometallic source of isotopically labeled functional groups. The reaction allows access to either un...

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Autores principales: Ton, Stephanie J., Ravn, Anne K., Hoffmann, Daniel Vrønning, Day, Craig S., Kingston, Lee, Elmore, Charles S., Skrydstrup, Troels
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10052257/
https://www.ncbi.nlm.nih.gov/pubmed/37006775
http://dx.doi.org/10.1021/jacsau.2c00708
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author Ton, Stephanie J.
Ravn, Anne K.
Hoffmann, Daniel Vrønning
Day, Craig S.
Kingston, Lee
Elmore, Charles S.
Skrydstrup, Troels
author_facet Ton, Stephanie J.
Ravn, Anne K.
Hoffmann, Daniel Vrønning
Day, Craig S.
Kingston, Lee
Elmore, Charles S.
Skrydstrup, Troels
author_sort Ton, Stephanie J.
collection PubMed
description [Image: see text] Herein, we report a strategy for the formation of isotopically labeled carboxylic esters from boronic esters/acids using a readily accessible palladium carboxylate complex as an organometallic source of isotopically labeled functional groups. The reaction allows access to either unlabeled or full (13)C- or (14)C-isotopically labeled carboxylic esters, and the method is characterized by its operational simplicity, mild conditions, and general substrate scope. Our protocol is further extended to a carbon isotope replacement strategy, involving an initial decarbonylative borylation procedure. Such an approach allows access to isotopically labeled compounds directly from the unlabeled pharmaceutical, which can have implications for drug discovery programs.
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spelling pubmed-100522572023-03-30 Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates Ton, Stephanie J. Ravn, Anne K. Hoffmann, Daniel Vrønning Day, Craig S. Kingston, Lee Elmore, Charles S. Skrydstrup, Troels JACS Au [Image: see text] Herein, we report a strategy for the formation of isotopically labeled carboxylic esters from boronic esters/acids using a readily accessible palladium carboxylate complex as an organometallic source of isotopically labeled functional groups. The reaction allows access to either unlabeled or full (13)C- or (14)C-isotopically labeled carboxylic esters, and the method is characterized by its operational simplicity, mild conditions, and general substrate scope. Our protocol is further extended to a carbon isotope replacement strategy, involving an initial decarbonylative borylation procedure. Such an approach allows access to isotopically labeled compounds directly from the unlabeled pharmaceutical, which can have implications for drug discovery programs. American Chemical Society 2023-02-13 /pmc/articles/PMC10052257/ /pubmed/37006775 http://dx.doi.org/10.1021/jacsau.2c00708 Text en © 2023 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Ton, Stephanie J.
Ravn, Anne K.
Hoffmann, Daniel Vrønning
Day, Craig S.
Kingston, Lee
Elmore, Charles S.
Skrydstrup, Troels
Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates
title Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates
title_full Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates
title_fullStr Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates
title_full_unstemmed Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates
title_short Rapid Access to Carbon-Isotope-Labeled Alkyl and Aryl Carboxylates Applying Palladacarboxylates
title_sort rapid access to carbon-isotope-labeled alkyl and aryl carboxylates applying palladacarboxylates
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10052257/
https://www.ncbi.nlm.nih.gov/pubmed/37006775
http://dx.doi.org/10.1021/jacsau.2c00708
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