2026-04-27T19:49:09Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/39122022-12-20T10:37:51Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

00925njm 22002777a 4500 dc Sanz Díez, Roberto author Miguel, Delia author Gohain, Mukut author García García, Patricia author Fernández Rodríguez, Manuel A. author González Pérez, Adán author Nieto Faza, Olalla . author Rodríguez de Lera, Ángel author Rodríguez, Félix author 2010-08 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 0947-6539 http://hdl.handle.net/10259/3912 10.1002/chem.201001162 gold homogeneous catalysis reaction mechanism DFT calculations indoles 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