Electrochemical low valent cobalt-catalyzed addition of aryl and vinyl chlorides to α-ketoamides <i>via</i> C–Cl bond activation
Prashant S. Shinde, Valmik S. Shinde, Magnus Rueping
Abstract
The development of an electrochemical cobalt catalyzed C-Cl bond activation at room temperature for the nucleophilic addition of aryl and vinyl chlorides to α-ketoamides is described. The overall method operates through an electrochemically induced low valent cobalt catalyst that oxidatively adds to aryl or vinyl chlorides affording medicinally important 3-hydroxy oxindole and 3-hydroxypyrrolidinone scaffolds. The development of an enantioselective version using a chiral pyrox ligand is also demonstrated.
Topics & Concepts
ElectrochemistryCobaltArylCatalysisChemistryEnantioselective synthesisNucleophilePolymer chemistryMedicinal chemistryOrganic chemistryAlkylElectrodePhysical chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques