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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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Detalles Bibliográficos
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
Descripción
Sumario:[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.