Mechanistic Studies on the Synthesis of Pyrrolidines and Piperidines via Copper-Catalyzed Intramolecular C–H Amination

We have recently developed a method for the synthesis of pyrrolidines and piperidines via intramolecular C–H amination of N-fluoride amides using [TpxCuL] complexes as precatalysts [Tpx = tris(pyrazolyl)borate ligand and L = THF or CH3CN]. Herein, we report mechanistic studies on this transformation...

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Detalles Bibliográficos
Autores: Muñoz Molina, José María, Bafaluy, Daniel, Funes Ardoiz, Ignacio, Aguirre, Adiran J. de, Maseras, Feliu, Rodríguez Belderraín, Tomás, Pérez Romero, Pedro José, Muñiz, Kilian
Tipo de recurso: artículo
Fecha de publicación:2022
País:España
Institución:Universidad de Huelva (UHU)
Repositorio:Arias Montano. Repositorio Institucional de la Universidad de Huelva
Idioma:inglés
OAI Identifier:oai:ariasmontano.uhu.es:10272/21255
Acceso en línea:http://hdl.handle.net/10272/21255
Access Level:acceso abierto
Palabra clave:Catalysts
Copper
Ligands
Organic reactions
Quantum mechanics
23 Química
Descripción
Sumario:We have recently developed a method for the synthesis of pyrrolidines and piperidines via intramolecular C–H amination of N-fluoride amides using [TpxCuL] complexes as precatalysts [Tpx = tris(pyrazolyl)borate ligand and L = THF or CH3CN]. Herein, we report mechanistic studies on this transformation, which includes the isolation and structural characterization of a fluorinated copper(II) complex, [(TpiPr2OH)CuF] [TpiPr = hydrotris(3,5-diisopropylpyrazolyl)borate], pertinent to the mechanistic pathway. The effects of the nature of the Tpx ligand in the copper catalyst as well as of the halide in the N–X amides employed as reactants have been investigated both from experimental and computational perspectives.

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