C–H Acylation as an Enabling Tool to Tag Phenolic Drugs

The site-selective functionalization of value-added compounds while implementing atom-economical C–H coupling partners represents an unmet challenge of utmost importance within organic synthesis. Herein, we report a Pd-catalyzed directed C–H acylation of a collection of relevant phenol-containing co...

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Detalles Bibliográficos
Autores: Girón Elola, Carlota, Correa Navarro, Arkaitz
Tipo de recurso: artículo
Fecha de publicación:2024
País:España
Institución:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/72266
Acceso en línea:http://hdl.handle.net/10810/72266
Access Level:acceso abierto
Palabra clave:drugs
acylation
palladium catalysis
Descripción
Sumario:The site-selective functionalization of value-added compounds while implementing atom-economical C–H coupling partners represents an unmet challenge of utmost importance within organic synthesis. Herein, we report a Pd-catalyzed directed C–H acylation of a collection of relevant phenol-containing compounds with ethanol and other alcohols and aldehydes. This tagging technique is distinguished by itswater compatibility and predictable regioselectivity and features the use of ethanol as renewable feed- stock for the modification of intricate phenols, including estrogens and other top-selling pharmaceuticals. Mechanistic studies support the intermediacy of a challenging 6-membered dimeric palladacycle that undergoes the addition of nucleophilic acyl radical species