Cobalt-Catalyzed ortho-C−H functionalization/alkyne annulation of benzylamine derivatives: Access to dihydroisoquinolines
A practical picolinamide-directed C−H functionalization/alkyne annulation of benzylamine derivatives enabling access to the previously elusive 1,4-dihydroisoquinoline skeleton was developed using molecular O2as the sole oxidant and Co(OAc)2as precatalyst. The method is compatible with both internal...
| Autores: | , , , |
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| Formato: | artículo |
| Fecha de publicación: | 2017 |
| País: | España |
| Recursos: | Universidad Autónoma de Madrid |
| Repositorio: | Biblos-e Archivo. Repositorio Institucional de la UAM |
| Idioma: | inglés |
| OAI Identifier: | oai:repositorio.uam.es:10486/685957 |
| Acesso em linha: | http://hdl.handle.net/10486/685957 https://dx.doi.org/10.1002/chem.201702283 |
| Access Level: | acceso abierto |
| Palavra-chave: | alkyne annulation cobalt dihydroisoquinoline picolinamide Química |
| Resumo: | A practical picolinamide-directed C−H functionalization/alkyne annulation of benzylamine derivatives enabling access to the previously elusive 1,4-dihydroisoquinoline skeleton was developed using molecular O2as the sole oxidant and Co(OAc)2as precatalyst. The method is compatible with both internal and terminal alkynes and shows high versatility and functional-group tolerance. Furthermore, full preservation of enantiopurity is observed when using non-racemic α-substituted benzylamine derivatives. Kinetic analysis of the reagents and catalyst, labeling experiments, and the isolation and identification of catalytically competent Co-complexes revealed important insights about the mechanism |
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