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dc.contributor.authorSuárez, Anisley 
dc.contributor.authorSuarez Pantiga, Samuel 
dc.contributor.authorNieto Faza, Olalla .
dc.contributor.authorSanz Díez, Roberto 
dc.date.accessioned2018-09-07T10:56:59Z
dc.date.available2018-10-06T02:45:06Z
dc.date.issued2017-10
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10259/4926
dc.description.abstractGold(III)-catalyzed cycloisomerization of α-bis(indol-3-yl)methyl alkynols selectively affords 1-(indol-3-yl)carbazoles, in a transformation that takes place through a selective 1,2-alkyl vs 1,2-vinyl migration step in the vinyl-gold intermediate generated from the initial 5-endo-spirocyclization. The reaction proceeds well with either tertiary or secondary starting alkynols as well as with a wide variety of alkyne substituents. The key role of the other indol-3-yl substituent for the unexpected selectivity in the 1,2 rearrangement has also been supported by DFT calculations that reveal a low barrier, two-step mechanism in the alkyl migration path where the second indole significantly stabilizes a carbocationic intermediate.en
dc.description.sponsorshipJunta de Castilla y León and FEDER (BU076U16) and Ministerio de Economía y Competitividad (MINECO) (CTQ2016-75023-C2-1-P and CTQ2016-75023- C2-2-P)en
dc.format.mimetypeapplication/pdf
dc.language.isoenges
dc.publisherAmerican Chemical Societyen
dc.relation.ispartofOrganic Letters. 2018, V. 19, n. 19, p. 5074–5077en
dc.subject.otherQuímica orgánicaes
dc.subject.otherChemistry, Organicen
dc.titleGold-Catalyzed Synthesis of 1-(Indol-3-yl)carbazoles: Selective 1,2-Alkyl vs 1,2-Vinyl Migrationen
dc.typeArtículoes
dc.typeinfo:eu-repo/semantics/article
dc.rights.accessRightsinfo:eu-repo/semantics/openAccess
dc.relation.publisherversionhttps://doi.org/10.1021/acs.orglett.7b02303
dc.identifier.doi10.1021/acs.orglett.7b02303
dc.relation.projectIDinfo:eu-repo/grantAgreement/JCyL/BU076U16
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/CTQ2016-75023-C2-1-P
dc.relation.projectIDinfo:eu-repo/grantAgreement/MINECO/CTQ2016-75023-C2-2-P
dc.type.hasVersioninfo:eu-repo/semantics/acceptedVersionen


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