Tridentate Nickel(II)-Catalyzed Chemodivergent C–H Functionalization and Cyclopropanation: Regioselective and Diastereoselective Access to Substituted Aromatic Heterocycles
Ekta Nag, Sai Manoj N. V. T. Gorantla, Selvakumar Arumugam, Aditya Kulkarni, Kartik Chandra Mondal, Sudipta Roy
Abstract
A Schiff-base nickel(II)-phosphene-catalyzed chemodivergent C-H functionalization and cyclopropanation of aromatic heterocycles is reported in moderate to excellent yields and very good regioselectivity and diastereoselectivity. The weak, noncovalent interaction between the phosphene ligand and Ni center facilitates the ligand dissociation, generating the electronically and coordinatively unsaturated active catalyst. The proposed mechanisms for the reported reactions are in good accord with the experimental results and theoretical calculations, providing a suitable model of stereocontrol for the cyclopropanation reaction.
Topics & Concepts
RegioselectivityCyclopropanationChemistryNickelCatalysisSurface modificationCombinatorial chemistryMedicinal chemistryOrganic chemistryPhysical chemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsAsymmetric Hydrogenation and Catalysis