Functional-Group-Tolerant, Silver-Catalyzed N–N Bond Formation by Nitrene Transfer to Amines
Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI=NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the c...
| Autores: | , , , , , , , , , |
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| Tipo de recurso: | artículo |
| Fecha de publicación: | 2017 |
| 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:10272/16191 |
| Acceso en línea: | http://hdl.handle.net/10272/16191 |
| Access Level: | acceso abierto |
| Palabra clave: | Catalyst Aminimides Nitrene |
| Sumario: | Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhI=NTs. Remarkably, this transformation proceeds in a selective manner in the presence of olefins and other functional groups without formation of the commonly observed aziridines or C-H insertion products. The methodology can be applied not only to rather simple tertiary amines but also to complex natural molecules such as brucine or quinine, where the products derived from N-N formation were exclusively formed. Theoretical mechanistic studies have shown that this selective Namidation reaction proceeds through triplet silver-nitrenes. |
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