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| dc.contributor.author | Sanz Díez, Roberto | |
| dc.contributor.author | Miguel, Delia | |
| dc.contributor.author | Martínez Cuezva, Alberto | |
| dc.contributor.author | Gohain, Mukut | |
| dc.contributor.author | García García, Patricia | |
| dc.contributor.author | Fernández Rodríguez, Manuel A. | |
| dc.contributor.author | Álvarez Manuel, Estela | |
| dc.contributor.author | Rodríguez, Félix | |
| dc.date.accessioned | 2015-10-01T10:36:21Z | |
| dc.date.available | 2015-10-01T10:36:21Z | |
| dc.date.issued | 2010-12 | |
| dc.identifier.issn | 1434-193X | |
| dc.identifier.uri | http://hdl.handle.net/10259/3864 | |
| dc.description.abstract | 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. | en |
| dc.description.sponsorship | 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. | en |
| dc.format.mimetype | application/pdf | |
| dc.language.iso | eng | es |
| dc.publisher | Wiley-VCH Verlag | en |
| dc.relation.ispartof | European Journal of Organic Chemistry. 2010. V. 2010, n. 36, p. 7027–7039 | en |
| dc.subject | Indoles | en |
| dc.subject | Alkylation | en |
| dc.subject | Brønsted acids | en |
| dc.subject | Alcohols | en |
| dc.subject | Nucleophilic substitution | en |
| dc.subject.other | Química orgánica | es |
| dc.subject.other | Chemistry, Organic | en |
| dc.title | Brønsted Acid Catalyzed Alkylation of Indoles with Tertiary Propargylic Alcohols: Scope and Limitations | en |
| dc.type | info:eu-repo/semantics/article | |
| dc.description.version | 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. | |
| dc.rights.accessRights | info:eu-repo/semantics/openAccess | |
| dc.relation.publisherversion | http://dx.doi.org/10.1002/ejoc.201001055 | |
| dc.identifier.doi | 10.1002/ejoc.201001055 | |
| dc.relation.projectID | info:eu-repo/grantAgreement/JCyL/BU021A09 | |
| dc.relation.projectID | info:eu-repo/grantAgreement/JCyL/GR-172 | |
| dc.relation.projectID | info:eu-repo/grantAgreement/MEC/SB2006-0215 | |
| dc.relation.projectID | info:eu-repo/grantAgreement/FEDER/CTQ2007-61436/BQU | |
| dc.relation.projectID | info:eu-repo/grantAgreement/FEDER/CTQ2009-09949/BQU | |
| dc.type.hasVersion | info:eu-repo/semantics/submittedVersion | en |
