Catalyst-Directed Selectivity in Vinylcarbene Reactions: A Comparative Study of Ag, Rh, and Cu Complexes

A comprehensive mechanistic investigation is conducted to uncover the factors governing the selectivity of Ag, Rh, and Cu catalysts in vinylcarbene-mediated reactions. The study examines the preference for carbenic versus vinylogous C(sp3)─H bond insertion, highlighting the critical roles of the ele...

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Detalles Bibliográficos
Autores: Monreal Corona, Roger, Díaz Jiménez, Àlex, Roglans, Anna, Poater, Albert, Pla Quintana, Anna, Pérez Romero, Pedro José, Caballero Bevia, Ana
Tipo de recurso: artículo
Fecha de publicación:2025
País:España
Institución:Universidad de Huelva (UHU)
Repositorio:Arias Montano. Repositorio Institucional de la Universidad de Huelva
Idioma:inglés
OAI Identifier:oai:ariasmontano.uhu.es:10272/27604
Acceso en línea:https://hdl.handle.net/10272/27604
Access Level:acceso abierto
Palabra clave:Alkynes
Carbenes
Carbenic reactivity
C─H functionalization
Density functional theory
Vinylogous reactivity
23 Química
Descripción
Sumario:A comprehensive mechanistic investigation is conducted to uncover the factors governing the selectivity of Ag, Rh, and Cu catalysts in vinylcarbene-mediated reactions. The study examines the preference for carbenic versus vinylogous C(sp3)─H bond insertion, highlighting the critical roles of the electronic and steric properties of transition metal catalysts. Contrary to previous assumptions that the enhanced electrophilic character of the vinylogous position in metal vinyl carbenes is the primary determinant, the findings demonstrate that the stereoelectronic effects of the ligand play a more dominant role. These insights inform the design of catalytic systems with tailored selectivity, advancing predictive catalysis and C─H bond functionalization.