Intermolecular α-Functionalization of Benzylamides with <i>N</i>-Nucleophiles via Oxidative Umpolung: Synthesis of Tetrasubstituted 3,3′-Oxindoles
Yue Wang, Yue Wang, Jin‐Tao Yu, Yang Wang, Yang Wang, Feng Shi
Abstract
A hypervalent iodine-mediated intermolecular α-umpolung reaction between α-aryl- or alkyl-substituted amides and benzotriazoles or purine derivatives as N -centered nucleophiles has been established. The reaction involves sequential intra/intermolecular oxidative C–N couplings in a controlled manner, affording tetrasubstituted 3,3′-oxindoles in moderate to good yields. This approach efficiently addresses the challenges in constructing tetrasubstituted carbon centers via α-umpolung functionalizations of carbonyl compounds and serves as a new strategy for synthesizing biologically important 3,3′-disubstituted oxindoles.
Topics & Concepts
UmpolungChemistryNucleophileSurface modificationIntermolecular forceCombinatorial chemistryOxidative phosphorylationOrganic chemistryStereochemistryCatalysisMoleculeBiochemistryPhysical chemistryCatalytic C–H Functionalization MethodsOxidative Organic Chemistry ReactionsSynthetic Organic Chemistry Methods