2026-04-29T11:59:30Zhttps://riubu.ubu.es/oai/request

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

00925njm 22002777a 4500 dc Sanz Díez, Roberto author Miguel, Delia author Martínez Cuezva, Alberto author Gohain, Mukut author García García, Patricia author Fernández Rodríguez, Manuel A. author Álvarez Manuel, Estela author Rodríguez, Félix author 2010-12 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. 1434-193X http://hdl.handle.net/10259/3864 10.1002/ejoc.201001055 Indoles Alkylation Brønsted acids Alcohols Nucleophilic substitution Brønsted Acid Catalyzed Alkylation of Indoles with Tertiary Propargylic Alcohols: Scope and Limitations