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oai:riubu.ubu.es:10259/37992021-11-10T09:38:24Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Solvent- and ligand-induced switch of selectivity in gold(I)-catalyzed tandem reactions of 3-propargylindoles Álvarez Manuel, Estela Miguel, Delia García García, Patricia Fernández Rodríguez, Manuel A. Rodríguez, Félix Sanz Díez, Roberto catalysis gold indoles Nazarov cyclizations selectivity Química orgánica Chemistry, Organic The selectivity of our previously described gold-catalyzed tandem reaction, 1,2-indole migration followed by aura-iso-Nazarov cyclization, of 3-propargylindoles bearing (hetero)aromatic substituents at both the propargylic and terminal positions, was reversed by the proper choice of the catalyst and the reaction conditions. Thus, 3-(inden-2-yl)indoles, derived from an aura-Nazarov cyclization (instead of an aura-iso-Nazarov cyclization), were obtained in moderate to good yields from a variety of 3-propargylindoles MICINN (CTQ2010-15358 and CTQ2009-09949), Junta de Castilla y Leon (BU021A09 and GR-172), MEC (FPU predoctoral fellowship to D.M.), Ramón y Cajal (contract to M.A F R.), Juan de la Cierva (contract to P.G.G.) 2015-07-27T09:55:12Z 2015-07-27T09:55:12Z 2011-06 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion 1860-5397 http://hdl.handle.net/10259/3799 10.3762/bjoc.7.89 eng Beilstein Journal of Organic Chemistry. 2011, v. 7, p. 786–793 Gold catalysis for organic synthesis http://dx.doi.org/10.3762/bjoc.7.89 info:eu-repo/grantAgreement/MICINN/CTQ2010-15358 info:eu-repo/grantAgreement/MICINN/CTQ2009-09949 info:eu-repo/grantAgreement/JCyL/BU021A09 info:eu-repo/grantAgreement/JCyL/GR-172 Attribution 4.0 International http://creativecommons.org/licenses/by/4.0/ Este documento está sujeto a una licencia de uso Creative Commons, por la cual está permitido hacer copia, distribuir, comunicar públicamente, remezclar, transformar y crear a partir del material para cualquier finalidad, incluso comercial, siempre que se cite al autor original, se proporcione un enlace a la licencia y se indique si se han realizado cambios info:eu-repo/semantics/openAccess application/pdf Beilstein-Institut https://riubu.ubu.es/bitstream/10259/3799/7/Beilstein_J._Org._Chem._2011.pdf.jpg Hispana TEXT http://creativecommons.org/licenses/by/4.0/ RIUBU. Repositorio Institucional de la Universidad de Burgos http://hdl.handle.net/10259/3799