Silyl Radical Mediated Cross-Electrophile Coupling of <i>N</i>-Acyl-imides with Alkyl Bromides under Photoredox/Nickel Dual Catalysis
Taline Kerackian, Antonio Reina, Didier Bouyssi, Nuno Monteiro, Abderrahmane Amgoune
Abstract
A photoredox Ni-catalyzed cross-coupling of N-acyl-imides with unactivated alkyl bromides has been developed that enables efficient access to a variety of functionalized alkyl ketones, including unsymmetrical dialkyl ketones, under very mild and operationally practical conditions. The reaction that operates without the need for any preformed carbon nucleophile proceeds via the combination of two different bond activation processes, i.e. Ni-catalyzed imide activation via C(acyl)–N bond cleavage and (TMS)3Si radical-mediated alkyl halide activation via halogen-atom abstraction.
Topics & Concepts
ChemistryAlkylNucleophileElectrophileCatalysisSilylationImideHalideBond cleavageHalogenPhotoredox catalysisPhotochemistryMedicinal chemistryOrganic chemistryPhotocatalysisRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques