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

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 2016-01-27T08:23:52Z 2016-01-27T08:23:52Z 2010-08 0947-6539 http://hdl.handle.net/10259/3912 10.1002/chem.201001162 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 MEC/FEDER (CTQ2007-61436/BQU) and Junta de Castilla y León (BU021A09) for financial support. We are also grateful to MEC (FPU predoctoral fellowship to D.M., “Young Foreign Researchers” contract (SB2006-0215) to M.G., “Ramón y Cajal” contract to M.A.F.-R., and “Juan de la Cierva” contract to P.G.-G.) and Fundación Ramón Areces (predoctoral fellowship to A.G.P.). This is the peer reviewed version of the following article: Sanz, R., Miguel, D., Gohain, M., García-García, P., Fernández-Rodríguez, Manuel A., González-Pérez, A., Nieto-Faza, O., de Lera, Ángel R. and Rodríguez, F. (2010), 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. Chem. Eur. J., 16: 9818–9828. doi:10.1002/chem.201001162, which has been published in final form at doi:10.1002/chem.201001162. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving application/pdf eng Wiley-VCH Verlag 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 gold homogeneous catalysis reaction mechanism DFT calculations indoles Química orgánica Chemistry, Organic 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 info:eu-repo/semantics/article info:eu-repo/semantics/acceptedVersion info:eu-repo/semantics/openAccess