Reductive molybdenum‐catalyzed direct amination of boronic acids with nitro compounds

The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has...

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Detalles Bibliográficos
Autores: Suarez Pantiga, Samuel, Hernández Ruiz, Raquel, Virumbrales, Cintia, Pedrosa Sáez, María de los Remedios, Sanz Díez, Roberto
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2019
País:España
Institución:Universidad de Burgos (UBU)
Repositorio:Repositorio Institucional de la Universidad de Burgos (RIUBU)
OAI Identifier:oai:riubu.ubu.es:10259/5178
Acceso en línea:http://hdl.handle.net/10259/5178
Access Level:acceso abierto
Palabra clave:amination
boronic acids
molybdenum
nitro compounds
reduction
Química orgánica
Chemistry, Organic
Descripción
Sumario:The synthesis of aromatic amines is of utmost importance in a wide range of chemical contexts. We report a direct amination of boronic acids with nitro compounds to yield (hetero)aryl amines. The novel combination of a dioxomolybdenum(VI) catalyst and triphenylphosphine as inexpensive reductant has revealed to be decisive to achieve this new C-N coupling. Our methodology has proven to be scalable, air and moisture tolerant, highly chemoselective and engages both aliphatic and aromatic nitro compounds. More-over, this general and step-economical synthesis of aromatic secondary amines show cases orthogonality to other aromatic secondary amines show cases orthogonality to other aromatic amine syntheses as it tolerates aryl halides and carbonyl compounds.