Characterization of a Silver Vinylcarbene Intermediate in Carbene−Alkyne Metathesis and Its Concerted C(sp2)−H Bond Insertion

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dc.contributor.authorDíaz Jiménez, Àlex
dc.contributor.authorPérez Romero, Pedro José
dc.contributor.authorCaballero Bevia, Ana
dc.contributor.authorPla Quintana, Anna
dc.date.accessioned2026-03-09T07:53:02Z
dc.date.available2026-03-09T07:53:02Z
dc.date.issued2025
dc.description.abstractHerein we present compelling evidence of the intervention of electrophilic silver vinylcarbenes in the carbene-alkyne metathesis (CAM) reaction, leading to a pivotal C(sp2)-H insertion process. The delicate equilibrium between the stability and reactivity of transient species is crucial for efficient detection. Through meticulous mechanistic exploration, we unveil that the mechanism for the C(sp2)-H insertion hinges on the substitution pattern. Indeed, it departs from the previously documented stepwise mechanism (involving Wheland intermediates), and it follows a concerted route, quite uncommon for this transformation.
dc.description.centerCIQSO
dc.description.departmentQuímica "Profesor José Carlos Vílchez Martín"
dc.description.sponsorshipThe authors are grateful for finantial support from ProjectsPID2021-127423NB-I00 to A.P., PID2020-113711GB-I00 and PID2023-146849NB-I00 to A.P.-Q., PID2019-106699GB-I00 to A.Co., PID2020-113797RB-C21 and PID2023-146946NB-I00 to P.J.P. and A.C. funded by the Ministerio de Ciencia, Innovación y Universidades of Spain MCIU/AEI/10.13039/501100011033 and FEDER, UE,; RED2022-134074-T and RED2022-134331-T for network support, and from the Generalitat de Catalunya (2021-SGR-623 to A.R., 2021SGR-475 to A.Co. projects). We thank the Spanish Ministerio de Universidades for the predoctoral fellowship FPU18/02912 to À.D.-J. and FPU20/00707 to R.M.-C. and the Catalan Government for the predoctoral fellowship 2022 FI_B 00605 to A.A.-N. and a Beatriu de Pinós-AGAUR Postdoctoral grant (2022BP00051) to A.S.. A.P.-Q., A. Co, and A.P. are Serra Húnter Fellows and A.P. and A.Co. thank ICREA Academia Prizes.
dc.identifier.citationDíaz-Jiménez, À., Monreal-Corona, R., Saha, A., Álvarez-Núñez, A., Company, A., Parella, T., Pérez, P. J., Caballero, A., Roglans, A., Poater, A., & Pla-Quintana, A. (2026). Characterization of a Silver Vinylcarbene Intermediate in Carbene–Alkyne Metathesis and Its Concerted C(sp2)–H Bond Insertion. Journal of the American Chemical Society, 148(3), 3689–3696. https://doi.org/10.1021/jacs.5c19806
dc.identifier.doi10.1021/jacs.5c19806
dc.identifier.issn0002-7863
dc.identifier.issn1520-5126 (electrónico)
dc.identifier.urihttps://hdl.handle.net/10272/28056
dc.language.isoeng
dc.publisherAmerican Chemical Society
dc.rightsAttribution 4.0 Internationalen
dc.rights.accessRightsopen access
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subject.otherCarbene compounds
dc.subject.otherCarbon
dc.subject.otherHydrocarbons
dc.subject.otherSilver
dc.subject.otherSubstituents
dc.subject.unesco2306 Química Orgánica
dc.subject.unesco2306.15 Mecanismos de Reacción
dc.titleCharacterization of a Silver Vinylcarbene Intermediate in Carbene−Alkyne Metathesis and Its Concerted C(sp2)−H Bond Insertion
dc.typejournal article
dc.type.hasVersionVoR
dspace.entity.typePublication
relation.isAuthorOfPublicationc6f8222a-d8d2-4736-baa6-4a2330bdf6b6
relation.isAuthorOfPublicationc0889099-8ac4-4aa5-b9b0-047f4fa34151
relation.isAuthorOfPublication.latestForDiscoveryc6f8222a-d8d2-4736-baa6-4a2330bdf6b6

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