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 PhINTs. 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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| Formato: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2017 |
| País: | España |
| Recursos: | 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:2072/335521 |
| Acesso em linha: | http://hdl.handle.net/2072/335521 https://doi.org/10.1021/jacs.6b08219 |
| Access Level: | acceso abierto |
| Palavra-chave: | 54 |
| Resumo: | Silver(I) promotes the highly chemoselective N-amidation of tertiary amines under catalytic conditions to form aminimides by nitrene transfer from PhINTs. 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 bond formation were exclusively formed. Theoretical mechanistic studies have shown that this selective N-amidation reaction proceeds through triplet silver nitrenes. |
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