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

Brønsted Acid Catalyzed Alkylation of Indoles with Tertiary Propargylic Alcohols: Scope and Limitations Sanz Díez, Roberto Miguel, Delia Martínez Cuezva, Alberto Gohain, Mukut García García, Patricia Fernández Rodríguez, Manuel A. Álvarez Manuel, Estela Rodríguez, Félix Indoles Alkylation Brønsted acids Alcohols Nucleophilic substitution 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. 2015-10-01T10:36:21Z 2015-10-01T10:36:21Z 2015-10-01T10:36:21Z 2010-12 info:eu-repo/semantics/article 1434-193X http://hdl.handle.net/10259/3864 10.1002/ejoc.201001055 eng 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 info:eu-repo/semantics/openAccess Wiley-VCH Verlag