Nickel‐Catalyzed Reductive Alkylation of Heteroaryl Imines**
Raymond F. Turro, Marco Brandstätter, Sarah E. Reisman
Abstract
Abstract The preparation of heterobenzylic amines by a Ni‐catalyzed reductive cross‐coupling between heteroaryl imines and C(sp 3 ) electrophiles is reported. This umpolung‐type alkylation proceeds under mild conditions, avoids the pre‐generation of organometallic reagents, and exhibits good functional group tolerance. Mechanistic studies are consistent with the imine substrate acting as a redox‐active ligand upon coordination to a low‐valent Ni center. The resulting bis(2‐imino)heterocycle⋅Ni complexes can engage in alkylation reactions with a variety of C(sp 3 ) electrophiles, giving heterobenzylic amine products in good yields.
Topics & Concepts
UmpolungElectrophileAlkylationChemistryImineReagentCatalysisLigand (biochemistry)Amine gas treatingReductive eliminationCombinatorial chemistryNickelSubstrate (aquarium)Medicinal chemistryNucleophileOrganic chemistryGeologyReceptorBiochemistryOceanographyCatalytic C–H Functionalization MethodsAsymmetric Hydrogenation and CatalysisCatalytic Cross-Coupling Reactions