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Native Amides as Enabling Vehicles for Forging sp <sup>3</sup> <i>–</i> sp <sup>3</sup> Architectures via Interrupted Deaminative Ni-Catalyzed Chain-Walking

Jesus Rodrigalvarez, Hao Wang, Rubén Martı́n

2023Journal of the American Chemical Society81 citationsDOIOpen Access PDF

Abstract

Herein, we disclose an interrupted deaminative Ni-catalyzed chain-walking strategy that forges sp 3 – sp 3 architectures at remote, yet previously unfunctionalized, methylene sp 3 C–H sites enabled by the presence of native amides. This protocol is characterized by its mild conditions and wide scope, including challenging substrate combinations. Site-selectivity can be dictated by a judicious choice of the ligand, thus offering an opportunity to enable sp 3 – sp 3 bond formations that are otherwise inaccessible in conventional chain-walking events.

Topics & Concepts

ChemistryChain (unit)Substrate (aquarium)Scope (computer science)CatalysisMethyleneCombinatorial chemistrySelectivityOrganic chemistryEcologyComputer scienceBiologyProgramming languagePhysicsAstronomyCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsAsymmetric Hydrogenation and Catalysis
Native Amides as Enabling Vehicles for Forging sp <sup>3</sup> <i>–</i> sp <sup>3</sup> Architectures via Interrupted Deaminative Ni-Catalyzed Chain-Walking | Litcius