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dc.contributor.authorSanz Díez, Roberto 
dc.contributor.authorMiguel, Delia 
dc.contributor.authorGohain, Mukut 
dc.contributor.authorGarcía García, Patricia
dc.contributor.authorFernández Rodríguez, Manuel A. 
dc.contributor.authorGonzález Pérez, Adán 
dc.contributor.authorNieto Faza, Olalla .
dc.contributor.authorRodríguez de Lera, Ángel
dc.contributor.authorRodríguez, Félix
dc.date.accessioned2016-01-27T08:23:52Z
dc.date.available2016-01-27T08:23:52Z
dc.date.issued2010-08
dc.identifier.issn0947-6539
dc.identifier.urihttp://hdl.handle.net/10259/3912
dc.description.abstractSimilar to propargylic carboxylates and sulphides, 3- propargylindoles undergo 1,2-indole migrations under cationic gold(I)- catalysis. The intermediate Aucarbenoid complex may evolve through different pathways depending on the substituents at the propargylic and terminal positions of the alkyne moiety. Thus, 3-indenylindole derivatives were easily obtained through formal iso- Nazarov or Nazarov cyclizations. DFT computations support the formation of an alkylidenecyclopropane intermediate that undergoes aura-iso-Nazarov or aura-Nazarov cyclizations upon torquoselective ring opening. In addition, 3-dienylindoles could be accessed when none of the referred pathways were accessible and so the intermediate Au-carbenoid complex evolved via a 1,2-CH insertion reaction. We have also demonstrated that the final products can be obtained in a one-pot protocol from easily available propargylic alcohols and indolesen
dc.description.sponsorshipMEC/FEDER (CTQ2007-61436/BQU) and Junta de Castilla y León (BU021A09) for financial support. We are also grateful to MEC (FPU predoctoral fellowship to D.M., “Young Foreign Researchers” contract (SB2006-0215) to M.G., “Ramón y Cajal” contract to M.A.F.-R., and “Juan de la Cierva” contract to P.G.-G.) and Fundación Ramón Areces (predoctoral fellowship to A.G.P.).en
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherWiley-VCH Verlagen
dc.relation.ispartofChemistry-A european journal. 2010, V. 16, n. 32, p. 9818-9828en
dc.subjectgolden
dc.subjecthomogeneous catalysisen
dc.subjectreaction mechanismen
dc.subjectDFT calculationsen
dc.subjectindolesen
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleSynthesis of diverse indole-containing scaffolds by gold(I)-catalyzed tandem reactions of 3-propargylindoles initiated by 1,2-indole migrations: scope and computational studiesen
dc.typeinfo:eu-repo/semantics/article
dc.description.versionThis is the peer reviewed version of the following article: Sanz, R., Miguel, D., Gohain, M., García-García, P., Fernández-Rodríguez, Manuel A., González-Pérez, A., Nieto-Faza, O., de Lera, Ángel R. and Rodríguez, F. (2010), Synthesis of Diverse Indole-Containing Scaffolds by Gold(I)-Catalyzed Tandem Reactions of 3-Propargylindoles Initiated by 1,2-Indole Migrations: Scope and Computational Studies. Chem. Eur. J., 16: 9818–9828. doi:10.1002/chem.201001162, which has been published in final form at doi:10.1002/chem.201001162. 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/chem.201001162
dc.identifier.doi10.1002/chem.201001162
dc.relation.projectIDinfo:eu-repo/grantAgreement/MEC-FEDER/CTQ2007-61436/BQU
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/BU021A09
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersionen


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