2024-03-29T15:46:48Zhttps://riubu.ubu.es/oai/requestoai: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