Nonplanar Tub-shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Molecularesgl
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánicagl
dc.contributor.authorBello García, Jesús
dc.contributor.authorPadín Santos, Damián
dc.contributor.authorVarela Carrete, Jesús Ángel
dc.contributor.authorSaá Rodríguez, Carlos
dc.date.accessioned2021-07-29T12:35:15Z
dc.date.issued2021
dc.descriptionNOTICE: This is the peer reviewed version of the following article: Bello-García, J., Padín, D., Varela, J. A., Saá, C. (2021). Nonplanar Tub-shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes. Org. Lett., 23, 14, 5539-5544. [doi: 10.1021/acs.orglett.1c01881]. This article may be used for non-commercial purposes in accordance with American Chemical Society Terms and Conditions for self-archivinggl
dc.description.abstractA novel tandem Ru-catalyzed [2 + 2 +2] cycloaddition of arylenynes to dihydrobiphenylenes followed by halogen-radical ring opening has been developed for the construction of tub-shaped halogenated benzocyclooctatetraenes (bCOTs). Cross-couplings and Diels-Alder reactions of the brominated bCOTs allow the formation of the corresponding eight-membered ring fused PAHs. The halogen-radical ring opening prob-ably occurs via a selective formation of a bis-allyl radical at the 1,3-cyclohexadiene moiety, halogenation at the bridgehead carbon and final electrocyclic ring opening.gl
dc.description.peerreviewedSIgl
dc.description.sponsorshipThis work has received financial support from MINECO (project CTQ2017-87939R and ORFEO-CINQA network RED2018-102387-T), the Xunta de Galicia (project ED431C 2018/04 and Centro singular de investigación de Galicia accreditation 2019-2022, ED431G 2019/03) and the European Union (European Regional Development Fund – ERDF). J.B. thanks Xunta de Galicia for a pre-doctoral contract. We are also grateful to the CESGA (Xunta de Gali-cia) for computational time.gl
dc.identifier.citationBello-García, J., Padín, D., Varela, J. A., Saá, C. (2021). Nonplanar Tub-shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes. Org. Lett., 23, 14, 5539-5544gl
dc.identifier.doi10.1021/acs.orglett.1c01881
dc.identifier.essn1523-7052
dc.identifier.issn1523-7060
dc.identifier.otherPMC8499027
dc.identifier.urihttp://hdl.handle.net/10347/26643
dc.language.isoenggl
dc.publisherAmerican Chemical Societygl
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-87939-R/ES/NUEVAS RUTAS CATALITICAS A PAHS (HIDROCARBUROS AROMATICOS POLICICLICOS) DOPADOS Y HETEROCICLOS BIOACTIVOSgl
dc.relation.publisherversionhttps://doi.org/10.1021/acs.orglett.1c01881gl
dc.rights© 2021 American Chemical Society. This is an open access article under the CC Attribution 4.0 International (CC BY 4.0) license (http://creativecommons.org/licenses/by/4.0/)gl
dc.rights.accessRightsopen accessgl
dc.subjectCyclooctatetraenesgl
dc.subjectDihydrobiphenylenesgl
dc.subjectCOT-PAHsgl
dc.subjectElectrocyclic ring openinggl
dc.subjectRadical halogenationgl
dc.titleNonplanar Tub-shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenesgl
dc.typejournal articlegl
dc.type.hasVersionVoRgl
dspace.entity.typePublication
relation.isAuthorOfPublicatione9be05f9-b5a3-405c-aaf6-4e32700dd21d
relation.isAuthorOfPublication2c024eb2-7698-4785-bd0c-518f70068330
relation.isAuthorOfPublication.latestForDiscoverye9be05f9-b5a3-405c-aaf6-4e32700dd21d

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