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dc.contributor.authorSanz Díez, Roberto 
dc.contributor.authorMiguel, Delia 
dc.contributor.authorMartínez Cuezva, Alberto 
dc.contributor.authorGohain, Mukut 
dc.contributor.authorGarcía García, Patricia
dc.contributor.authorFernández Rodríguez, Manuel A. 
dc.contributor.authorÁlvarez Manuel, Estela 
dc.contributor.authorRodríguez, Félix
dc.date.accessioned2015-10-01T10:36:21Z
dc.date.available2015-10-01T10:36:21Z
dc.date.issued2010-12
dc.identifier.issn1434-193X
dc.identifier.urihttp://hdl.handle.net/10259/3864
dc.description.abstractDirect 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.sponsorshipJunta 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.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherWiley-VCH Verlagen
dc.relation.ispartofEuropean Journal of Organic Chemistry. 2010. V. 2010, n. 36, p. 7027–7039en
dc.subjectIndolesen
dc.subjectAlkylationen
dc.subjectBrønsted acidsen
dc.subjectAlcoholsen
dc.subjectNucleophilic substitutionen
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleBrønsted Acid Catalyzed Alkylation of Indoles with Tertiary Propargylic Alcohols: Scope and Limitationsen
dc.typeinfo:eu-repo/semantics/article
dc.description.versionThis 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.accessRightsinfo:eu-repo/semantics/openAccess
dc.relation.publisherversionhttp://dx.doi.org/10.1002/ejoc.201001055
dc.identifier.doi10.1002/ejoc.201001055
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/BU021A09
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/GR-172
dc.relation.projectIDinfo:eu-repo/grantAgreement/MEC/SB2006-0215
dc.relation.projectIDinfo:eu-repo/grantAgreement/FEDER/CTQ2007-61436/BQU
dc.relation.projectIDinfo:eu-repo/grantAgreement/FEDER/CTQ2009-09949/BQU
dc.type.hasVersioninfo:eu-repo/semantics/submittedVersionen


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