Base-Promoted Cobalt-Catalyzed Regio- and Enantioselective <i>para</i>-Friedel–Crafts Alkylation of Aniline Derivatives
Jia Zhou, Zihao Li, Le Wang, Jun‐Chen Kang, Xun-Hui Wang, Shu‐Yu Zhang
Abstract
Herein we disclose a highly efficient enantioselective para-C–H alkylation of aniline derivatives promoted by a base/Co/indeno-pybox ligand system. This methodology leads to the efficient construction of a series of enantioenriched aniline derivatives bearing all-carbon quaternary stereocenters. In addition, several special biologically or medicinally active indoles are facilely synthesized by our Co-catalyzed asymmetry synthesis method. Density functional theory calculations and experiment results suggest that the (acac)− anion of Co(acac)2 plays a very important role in chiral control during the nucleophilic reaction.
Topics & Concepts
StereocenterChemistryAnilineEnantioselective synthesisAlkylationNucleophileCatalysisCombinatorial chemistryCobaltBase (topology)Ligand (biochemistry)Organic chemistryReceptorMathematical analysisBiochemistryMathematicsCatalytic C–H Functionalization MethodsSynthesis and Catalytic ReactionsSynthesis of Indole Derivatives