2026-06-29T19:09:43Zhttps://riubu.ubu.es/oai/request

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

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 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 gold homogeneous catalysis reaction mechanism DFT calculations indoles 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 2016-01-27T08:23:52Z 2016-01-27T08:23:52Z 2010-08 info:eu-repo/semantics/article 0947-6539 http://hdl.handle.net/10259/3912 10.1002/chem.201001162 eng Chemistry-A european journal. 2010, V. 16, n. 32, p. 9818-9828 http://dx.doi.org/10.1002/chem.201001162 info:eu-repo/grantAgreement/MEC-FEDER/CTQ2007-61436/BQU info:eu-repo/grantAgreement/JCyL/BU021A09 info:eu-repo/semantics/openAccess Wiley-VCH Verlag