Organocatalytic N-formylation of amines by CO2 in batch and continuous flow

A continuous flow organocatalytic synthesis of formamides has been developed using amines and CO2 reaction partners in the presence of a silane reductant. The process is conducted under comparatively mild reaction conditions and allows the preparation of a broad family of N-substituted formamides in...

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Detalles Bibliográficos
Autores: Zanda, Nicola, Primitivo, Ludovica, Chaudari, Moreshwar, Kleij, Arjan W., Pericàs, Miquel A.
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2022
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/532765
Acceso en línea:http://hdl.handle.net/2072/532765
https://doi.org/10.1039/d2qo01711c
Access Level:acceso abierto
Palabra clave:Química
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Descripción
Sumario:A continuous flow organocatalytic synthesis of formamides has been developed using amines and CO2 reaction partners in the presence of a silane reductant. The process is conducted under comparatively mild reaction conditions and allows the preparation of a broad family of N-substituted formamides in good yield. The heterogenized catalyst is a PS-supported superbase (DBU), while (MeO)3SiH proved to be the most efficient reductant. The reaction was first optimized in batch mode, giving access to fifteen different N-substituted formamide products. The optimized conditions were then used as input to develop a proof-of-concept continuous flow process based on the model substrate N-phenyl aniline thereby providing N methyl-N-phenyl formamide as target with good productivity.