Synthesis of diverse indole-containing scaffolds by gold(I)-catalyzed tandem reactions of 3-propargylindoles initiated by 1,2-indole migrations: scope and computational studies
Similar to propargylic carboxylates and sulphides, 3- propargylindoles undergo 1,2-indole migrations under cationic gold(I)- catalysis. The intermediate Aucarbenoid complex may evolve through different pathways depending on the substituents at the propargylic and terminal positions of the alkyne moi...
| Autores: | , , , , , , , , |
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| Tipo de recurso: | artículo |
| Estado: | Versión aceptada para publicación |
| Fecha de publicación: | 2010 |
| País: | España |
| Institución: | Universidad de Burgos (UBU) |
| Repositorio: | Repositorio Institucional de la Universidad de Burgos (RIUBU) |
| OAI Identifier: | oai:riubu.ubu.es:10259/3912 |
| Acceso en línea: | http://hdl.handle.net/10259/3912 |
| Access Level: | acceso abierto |
| Palabra clave: | gold homogeneous catalysis reaction mechanism DFT calculations indoles Química orgánica Chemistry, Organic |
| Sumario: | Similar to propargylic carboxylates and sulphides, 3- propargylindoles undergo 1,2-indole migrations under cationic gold(I)- catalysis. The intermediate Aucarbenoid complex may evolve through different pathways depending on the substituents at the propargylic and terminal positions of the alkyne moiety. Thus, 3-indenylindole derivatives were easily obtained through formal iso- Nazarov or Nazarov cyclizations. DFT computations support the formation of an alkylidenecyclopropane intermediate that undergoes aura-iso-Nazarov or aura-Nazarov cyclizations upon torquoselective ring opening. In addition, 3-dienylindoles could be accessed when none of the referred pathways were accessible and so the intermediate Au-carbenoid complex evolved via a 1,2-CH insertion reaction. We have also demonstrated that the final products can be obtained in a one-pot protocol from easily available propargylic alcohols and indoles |
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