Regiodivergent sp3 C–H Functionalization via Ni-Catalyzed Chain-Walking Reactions

The catalytic translocation of a metal catalyst along a saturated hydrocarbon side chain constitutes a powerful strategy for enabling bond-forming reactions at remote, yet previously unfunctionalized, sp3 C–H sites. In recent years, Ni-catalyzed chain-walking reactions have offered counterintuitive...

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Detalles Bibliográficos
Autores: Rodrigalvarez, Jesus, Haut, Franz-Lucas, Martin, Ruben
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:España
Institución:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repositorio:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:2072/537176
Acceso en línea:http://hdl.handle.net/2072/537176
https://doi.org/10.1021/jacsau.3c00617
Access Level:acceso abierto
Palabra clave:Química
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Descripción
Sumario:The catalytic translocation of a metal catalyst along a saturated hydrocarbon side chain constitutes a powerful strategy for enabling bond-forming reactions at remote, yet previously unfunctionalized, sp3 C–H sites. In recent years, Ni-catalyzed chain-walking reactions have offered counterintuitive strategies for forging sp3 architectures that would be difficult to accomplish otherwise. Although these strategies have evolved into mature tools for advanced organic synthesis, it was only recently that chemists showed the ability to control the motion at which the catalyst “walks” throughout the alkyl chain. Specialized ligand backbones, additives and a judicious choice of noninnocent functional groups on the side chain have allowed the design of “a la carte” protocols that enable regiodivergent bond-forming scenarios at different sp3 C–H sites with distinct topological surface areas. Given the inherent interest in increasing the fraction of sp3 hybridized carbons in medicinal chemistry, Ni-catalyzed regiodivergent chain-walking reactions might expedite the access to target leads in drug discovery campaigns.