2026-08-29T14:42:49Zhttps://riubu.ubu.es/oai/request

oai:riubu.ubu.es:10259/38642022-12-19T13:14:34Zcom_10259_3593com_10259_5086com_10259_2604col_10259_3594

Sanz Díez, Roberto Miguel, Delia Martínez Cuezva, Alberto Gohain, Mukut García García, Patricia Fernández Rodríguez, Manuel A. Álvarez Manuel, Estela Rodríguez, Félix 2015-10-01T10:36:21Z 2015-10-01T10:36:21Z 2010-12 1434-193X http://hdl.handle.net/10259/3864 10.1002/ejoc.201001055 Direct alkylation of indoles with a wide variety of tertiary propargylic alcohols under Brønsted acid catalysis conditions has been studied. A general and environmentally friendly method for the synthesis of 3-propargylated indoles with quaternary carbon atoms at their propargylic positions has been developed. The reactions are highly regioselective with regard both to the indole and to the alkynol components. Only with N-unsubstituted 2-arylindoles do competitive SN′ reactions take place to afford 3-dienyl- or 3-allenylindoles, depending on the alkynol moiety. The reactions were carried out in air with undried solvents, and water was the only side product. Junta de Castilla y Leon (BU021A09 and GR-172) and the Ministerio de Educacion y Ciencia (MEC) and FEDER (CTQ2007-61436/BQU and CTQ2009-09949/BQU) for financial support. D. M. and A. M. thank the MEC for MEC-FPU predoctoral fellowships. M. G. thanks the MEC for a "Young Foreign Researchers" contract (SB2006-0215). M. A. F.-R. and P. G.-G. also thank the MEC for "Ramon y Cajal" and "Juan de la Cierva" contracts. This is the pre-peer reviewed version of the following article: Sanz, R., Miguel, D., Martínez, A., Gohain, M., García-García, P., Fernández-Rodríguez, M. A., Álvarez, E. and Rodríguez, F. (2010), Brønsted Acid Catalyzed Alkylation of Indoles with Tertiary Propargylic Alcohols: Scope and Limitations. Eur. J. Org. Chem., 2010: 7027–7039. doi: 10.1002/ejoc.201001055, which has been published in final form at 10.1002/ejoc.201001055. 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 European Journal of Organic Chemistry. 2010. V. 2010, n. 36, p. 7027–7039 http://dx.doi.org/10.1002/ejoc.201001055 info:eu-repo/grantAgreement/JCyL/BU021A09 info:eu-repo/grantAgreement/JCyL/GR-172 info:eu-repo/grantAgreement/MEC/SB2006-0215 info:eu-repo/grantAgreement/FEDER/CTQ2007-61436/BQU info:eu-repo/grantAgreement/FEDER/CTQ2009-09949/BQU Indoles Alkylation Brønsted acids Alcohols Nucleophilic substitution Química orgánica Chemistry, Organic Brønsted Acid Catalyzed Alkylation of Indoles with Tertiary Propargylic Alcohols: Scope and Limitations info:eu-repo/semantics/article info:eu-repo/semantics/submittedVersion info:eu-repo/semantics/openAccess