Cargando…
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...
Autores principales: | , , , , , , |
---|---|
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 |
_version_ | 1785015117830684672 |
---|---|
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. |
format | Online Article Text |
id | pubmed-10052257 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2023 |
publisher | American Chemical Society |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT tonstephaniej rapidaccesstocarbonisotopelabeledalkylandarylcarboxylatesapplyingpalladacarboxylates AT ravnannek rapidaccesstocarbonisotopelabeledalkylandarylcarboxylatesapplyingpalladacarboxylates AT hoffmanndanielvrønning rapidaccesstocarbonisotopelabeledalkylandarylcarboxylatesapplyingpalladacarboxylates AT daycraigs rapidaccesstocarbonisotopelabeledalkylandarylcarboxylatesapplyingpalladacarboxylates AT kingstonlee rapidaccesstocarbonisotopelabeledalkylandarylcarboxylatesapplyingpalladacarboxylates AT elmorecharless rapidaccesstocarbonisotopelabeledalkylandarylcarboxylatesapplyingpalladacarboxylates AT skrydstruptroels rapidaccesstocarbonisotopelabeledalkylandarylcarboxylatesapplyingpalladacarboxylates |