Au(I) as a π‑Lewis Base Catalyst: Controlled Synthesis of Sterically Congested Bis(triflyl)enals from α‑Allenols

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dc.contributor.authorToledano Pinedo, Mireia
dc.contributor.authorMartínez Del Campo, Teresa
dc.contributor.authorYanai, Hikaru
dc.contributor.authorAlmendros, Pedro
dc.date.accessioned2024-06-13T15:49:34Z
dc.date.available2024-06-13T15:49:34Z
dc.date.issued2022-09-12
dc.description.abstractA gold-catalyzed bis[(trifluoromethyl)sulfonyl]ethylation of α-allenols, which allows the preparation of sterically congested bis(triflyl)enals bearing quaternary carbon centers, is presented. This sequence differs from the conventional reaction pathway of α-allenols under π-acid catalysis, because in our case Au(I) functions as a π-Lewis base catalyst rather than a π-Lewis acid to activate the allene, facilitating the unusual addition of a carbon nucleophile of the gold complex belonging to the allenol moiety. Density functional theory calculations were carried out to understand this uncommon pathway.
dc.description.departmentDepto. de Química Orgánica
dc.description.facultyFac. de Ciencias Químicas
dc.description.refereedTRUE
dc.description.statuspub
dc.identifier.citationMireia Toledano-Pinedo, Teresa Martínez del Campo, Hikaru Yanai, and Pedro Almendros ACS Catalysis 2022 12 (19), 11675-11681 DOI: 10.1021/acscatal.2c03858
dc.identifier.doi10.1021/acscatal.2c03858
dc.identifier.officialurlhttps://doi.org/10.1021/acscatal.2c03858
dc.identifier.urihttps://hdl.handle.net/20.500.14352/104913
dc.issue.number19
dc.journal.titleACS Catalysis
dc.language.isoeng
dc.page.final11681
dc.page.initial11675
dc.publisherACS Publications
dc.rightsAttribution 4.0 Internationalen
dc.rights.accessRightsopen access
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subject.cdu547
dc.subject.keywordallenes
dc.subject.keywordgold π-Lewis base catalyst
dc.subject.keywordquaternary center
dc.subject.keywordselectivity
dc.subject.ucmCiencias
dc.subject.unesco23 Química
dc.titleAu(I) as a π‑Lewis Base Catalyst: Controlled Synthesis of Sterically Congested Bis(triflyl)enals from α‑Allenols
dc.typejournal article
dc.type.hasVersionVoR
dc.volume.number12
dspace.entity.typePublication
relation.isAuthorOfPublicationcc1cf4f2-577a-41ea-9854-93e787f6e1f6
relation.isAuthorOfPublication.latestForDiscoverycc1cf4f2-577a-41ea-9854-93e787f6e1f6
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