Universidad de Burgos Repositorio Repositorio
Por favor, use este identificador para citar o enlazar este ítem: http://hdl.handle.net/10259/3912

Ver estadísticas de uso
Título : 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
Autor : Sanz Díez, Roberto
Miguel, Delia
Gohain, Mukut
García García, Patricia
Fernández Rodríguez, Manuel A.
González Pérez, Adán
Nieto Faza, Olalla
Rodríguez de Lera, Ángel
Rodríguez, Félix
Publicado en: Chemistry-A european journal. 2010, V. 16, n. 32, p. 9818-9828
Editorial : Wiley-VCH Verlag
Fecha de publicación : ago-2010
ISSN : 0947-6539
DOI: 10.1002/chem.201001162
Resumen : 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-CH 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
Palabras clave: gold
homogeneous catalysis
reaction mechanism
DFT calculations
indoles
Materia: Química orgánica
Chemistry, Organic
URI : http://hdl.handle.net/10259/3912
Versión del editor: http://dx.doi.org/10.1002/chem.201001162
Aparece en las colecciones: Artículos SINTORG

Ficheros en este ítem:

Fichero Descripción Tamaño Formato
Sanz-Chem. Eur. J._2010.pdf533,59 kBAdobe PDFVisualizar/Abrir

Los ítems del Repositorio Institucional de la Universidad de Burgos están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.

 

Valid XHTML 1.0! DSpace Software Copyright © 2002-2008 MIT and Hewlett-Packard - Sobre DSpace