Toward 2-Thiophyne: ketocarbene versus hetaryne intermediates from 2-(Trimethylsilyl)thiophen-3-yl Triflate

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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.authorPozo Míguez, Iago
dc.contributor.authorCobas Martínez, Agustín
dc.contributor.authorPeña Gil, Diego
dc.contributor.authorGuitián Rivera, Enrique
dc.contributor.authorPérez Meirás, María Dolores
dc.date.accessioned2022-08-09T10:05:48Z
dc.date.available2022-08-09T10:05:48Z
dc.date.issued2021
dc.description.abstractThe reaction of 2-(trimethylsilyl)thiophen-3-yl triflate with CsF in the presence of 2,3,4,5-tetraphenylcyclopentadienone affords 4,5,6,7-tetraphenylbenzo[b]thiophene, as it would be expected from the hypothesized generation and trapping of 2-thiophyne. However, a detailed experimental and computational study discards the intermediacy of this elusive 5-membered hetaryne. Instead, a complex mechanism involving the generation of an intermediate ketocarbene, which adds to the cyclopentadienone to give an isolable tricyclic intermediate, followed by thermal rearrangements, is proposedgl
dc.description.peerreviewedSIgl
dc.description.sponsorshipFinancial support from the Spanish Agencia Estatal de Investigación (Nos. PID2019-110037GB-I00 and PCI2019-111933-2), the European Union’s Horizon 2020 (FET-Open project, Grant No. 863098), the Xunta de Galicia (No. ED431C 2020/22 and Centro Singular de Investigación de Galicia accreditation 2019-2022, ED431G 2019/03) and the European Union (European Regional Development Fund-ERDF, is gratefully acknowledged. The authors thank the Centro de Supercomputación de Galicia (CESGA) for generous allocation of computer time. I.P. thanks Xunta de Galicia and the European Union (European Social Fund, ESF) for the award of a predoctoral fellowshipgl
dc.identifier.citationOrg. Lett. 2021, 23, 7376−7380. https://doi.org/10.1021/acs.orglett.1c02552gl
dc.identifier.doi10.1021/acs.orglett.1c02552
dc.identifier.issn1523-7060
dc.identifier.urihttp://hdl.handle.net/10347/29041
dc.language.isoenggl
dc.publisherACS Publicationsgl
dc.relation.publisherversionhttps://doi.org/10.1021/acs.orglett.1c02552gl
dc.rights© 2021 The Authors. Published by American Chemical Society. This work is licenced under a Creative Commons Attribution 4.0 International licence (https://creativecommons.org/licenses/by/4.0/legalcode)gl
dc.rightsAtribución 4.0 Internacional
dc.rights.accessRightsopen accessgl
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectAdductsgl
dc.subjectCentral nervous systemgl
dc.subjectChemical reactionsgl
dc.subjectPrecursorsgl
dc.subjectRearrangementgl
dc.titleToward 2-Thiophyne: ketocarbene versus hetaryne intermediates from 2-(Trimethylsilyl)thiophen-3-yl Triflategl
dc.typejournal articlegl
dc.type.hasVersionVoRgl
dspace.entity.typePublication
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relation.isAuthorOfPublication.latestForDiscovery94d1f166-ab73-419e-acdb-2b94a9e54224

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