Artículo
Broad-Scope Amination of Aryl Sulfamates Catalyzed by a Palladium Phosphine Complex
Autor/es | Monti, Andrea
López Serrano, Joaquín Prieto Cárdenas, María Auxiliadora Nicasio Jaramillo, María del Carmen |
Departamento | Universidad de Sevilla. Departamento de Química Inorgánica |
Fecha de publicación | 2023-08-03 |
Fecha de depósito | 2024-01-30 |
Publicado en |
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Resumen | Among phenol-derived electrophiles, aryl sulfamates are attractive substrates since they can be employed as directing groups for C–H functionalization prior to catalysis. However, their use in C–N coupling is limited only ... Among phenol-derived electrophiles, aryl sulfamates are attractive substrates since they can be employed as directing groups for C–H functionalization prior to catalysis. However, their use in C–N coupling is limited only to Ni catalysis. Here, we describe a Pd-based catalyst with a broad scope for the amination of aryl sulfamates. We show that the N-methyl-2-aminobiphenyl palladacycle supported by the PCyp2ArXyl2 ligand (Cyp = cyclopentyl; ArXyl2 = 2,6-bis(2,6-dimethylphenyl)phenyl) efficiently catalyzes the C–N coupling of aryl sulfamates with a variety of nitrogen nucleophiles, including anilines, primary and secondary alkyl amines, heteroaryl amines, N-heterocycles, and primary amides. DFT calculations support that the oxidative addition of the aryl sulfamate is the rate-determining step. The C–N coupling takes place through a cationic pathway in the polar protic medium. |
Agencias financiadoras | Junta de Andalucía Ministerio de Ciencia e Innovación (MICIN). España Agencia Estatal de Investigación. España Universidad de Sevilla European Commission (EC). Fondo Europeo de Desarrollo Regional (FEDER) |
Identificador del proyecto | P20_00624
PID2020-113797RB-C22 US-1262266 |
Cita | Monti, A., López Serrano, J., Prieto Cárdenas, M.A. y Nicasio Jaramillo, M.d.C. (2023). Broad-Scope Amination of Aryl Sulfamates Catalyzed by a Palladium Phosphine Complex. ACS Catalysis, 13 (16), 10945-10952. https://doi.org/10.1021/acscatal.3c03166. |
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