Directed Palladium Catalyzed C−H (Ethoxycarbonyl)difluoromethylthiolation Reactions

The unprecedented Pd‐catalyzed (ethoxycarbonyl)difluoromethylthiolation reaction of various unsaturated derivatives was studied. In the presence of the (ethoxycarbonyl)difluoromethylsulfenamide reagent I and under mild reaction conditions (60 °C), both 2‐(hetero)aryl and 2‐(α‐aryl‐vinyl)pyridine der...

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Detalles Bibliográficos
Autores principales: Doche, Floriane, Escudero, Julien, Petit‐Cancelier, Fabien, Xiong, Heng‐Ying, Couve‐Bonnaire, Samuel, Audisio, Davide, Poisson, Thomas, Besset, Tatiana
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2022
Materias:
Research Articles
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9826264/
https://www.ncbi.nlm.nih.gov/pubmed/35904010
http://dx.doi.org/10.1002/chem.202202099
Descripción
Sumario:The unprecedented Pd‐catalyzed (ethoxycarbonyl)difluoromethylthiolation reaction of various unsaturated derivatives was studied. In the presence of the (ethoxycarbonyl)difluoromethylsulfenamide reagent I and under mild reaction conditions (60 °C), both 2‐(hetero)aryl and 2‐(α‐aryl‐vinyl)pyridine derivatives were smoothly functionalized with this methodology (37 examples, up to 87 % yield). Moreover, the synthetic interest of this fluorinated moiety was further showcased by its conversion into various original fluorinated residues. Finally, a plausible mechanism for this transformation was suggested.

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