2026-04-29T09:32:28Zhttps://riubu.ubu.es/oai/request

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

Sanz Díez, Roberto 531 500 0000-0003-2830-0892 Miguel, Delia 368 500 Gohain, Mukut 235 500 García García, Patricia 0c6817a7-07ab-499f-877c-c534362475cd 500 Fernández Rodríguez, Manuel A. 174 500 González Pérez, Adán 257 600 Nieto Faza, Olalla . 22ecaaeb-839e-4c87-89aa-1aff3dc73b53 500 Rodríguez de Lera, Ángel b22e3e44-1f79-495b-9a9b-1f07b8fe4dd3 500 Rodríguez, Félix bd204e31-71db-407f-8054-c7acbccad8bf 500 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 THUMBNAIL Sanz-Chem. Eur. J._2010.pdf.jpg Sanz-Chem. Eur. J._2010.pdf.jpg IM Thumbnail image/jpeg 4663 https://riubu.ubu.es/bitstream/10259/3912/4/Sanz-Chem.%20Eur.%20J._2010.pdf.jpg 96949421915b98f6eb4dc874e0d09d17 MD5 4 ORIGINAL Sanz-Chem. Eur. J._2010.pdf Sanz-Chem. Eur. J._2010.pdf application/pdf 546395 https://riubu.ubu.es/bitstream/10259/3912/1/Sanz-Chem.%20Eur.%20J._2010.pdf 7ee8e37cac1f1a223837109c0266cb00 MD5 1 LICENSE license.txt license.txt text/plain; charset=utf-8 1362 https://riubu.ubu.es/bitstream/10259/3912/2/license.txt 5d013bfa6e473ff0db22cd82a4d71a70 MD5 2 TEXT Sanz-Chem. Eur. J._2010.pdf.txt Sanz-Chem. Eur. J._2010.pdf.txt Extracted text text/plain 61091 https://riubu.ubu.es/bitstream/10259/3912/3/Sanz-Chem.%20Eur.%20J._2010.pdf.txt 1d971de61eb03937a5897f4d7d50b1e9 MD5 3 10259/3912 oai:riubu.ubu.es:10259/3912 2022-12-20 11:37:51.527 Repositorio Institucional de la Universidad de Burgos bubrep@ubu.es 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