title: 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.
abstract: Similar to propargylic carboxylates and sulphides, 3-propargylindoles undergo 1,2-indole migrations under cationic gold(I) catalysis. The intermediate Au-carbenoid 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 gold-iso-Nazarov or gold-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.
authors.affiliation: Area de Química Orgánica, Departamento de Química, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, Spain. rsd@ubu.es
authors.forename: Roberto
authors.initials: R
authors.lastname: Sanz
authors.forename: Delia
authors.initials: D
authors.lastname: Miguel
authors.forename: Mukut
authors.initials: M
authors.lastname: Gohain
authors.forename: Patricia
authors.initials: P
authors.lastname: García-García
authors.forename: Manuel A
authors.initials: MA
authors.lastname: Fernández-Rodríguez
authors.forename: Adán
authors.initials: A
authors.lastname: González-Pérez
authors.forename: Olalla
authors.initials: O
authors.lastname: Nieto-Faza
authors.forename: Angel R
authors.initials: AR
authors.lastname: de Lera
authors.forename: Félix
authors.initials: F
authors.lastname: Rodríguez