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Updated: Jan 13, 2026

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Characterization of a Silver Vinylcarbene Intermediate in Carbene-Alkyne Metathesis and Its Concerted C(sp2)-H Bond
Àlex Díaz-Jiménez1, Roger Monreal-Corona1, Arijit Saha1
1Institut de Química Computacional i Catàlisi (IQCC) and Departament de Química, Universitat de Girona (UdG), Facultat de Ciències, C/Maria Aurèlia Capmany, 69, Girona 17003, Catalunya, Spain.
Abstract:
Herein 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.
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