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dc.contributor.author | Bello García, Jesús |
dc.contributor.author | Padín Santos, Damián |
dc.contributor.author | Varela Carrete, Jesús Ángel |
dc.contributor.author | Saá Rodríguez, Carlos |
dc.date.accessioned | 2021-07-29T12:35:15Z |
dc.date.issued | 2021 |
dc.identifier.citation | 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 |
dc.identifier.issn | 1523-7060 |
dc.identifier.other | PMC8499027 |
dc.identifier.uri | http://hdl.handle.net/10347/26643 |
dc.description | NOTICE: 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-archiving |
dc.description.abstract | A 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. |
dc.description.sponsorship | This 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. |
dc.language.iso | eng |
dc.publisher | American Chemical Society |
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/) |
dc.subject | Cyclooctatetraenes |
dc.subject | Dihydrobiphenylenes |
dc.subject | COT-PAHs |
dc.subject | Electrocyclic ring opening |
dc.subject | Radical halogenation |
dc.title | Nonplanar Tub-shaped Benzocyclooctatetraenes via Halogen-Radical Ring Opening of Dihydrobiphenylenes |
dc.type | journal article |
dc.identifier.doi | 10.1021/acs.orglett.1c01881 |
dc.relation.publisherversion | https://doi.org/10.1021/acs.orglett.1c01881 |
dc.type.hasVersion | VoR |
dc.identifier.essn | 1523-7052 |
dc.rights.accessRights | open access |
dc.contributor.affiliation | Universidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares |
dc.contributor.affiliation | Universidade de Santiago de Compostela. Departamento de Química Orgánica |
dc.description.peerreviewed | SI |
dc.relation.projectID | info: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 BIOACTIVOS |
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