Palladium-Catalyzed Secondary Benzylic Imidoylative Reactions
Chenglong Wang, Licheng Wu, Wentao Xu, Feng He, Jingping Qü, Yifeng Chen
Abstract
Reported herein is a palladium-catalyzed secondary benzylic imidoylative Negishi reaction leveraging the sterically bulky aromatic isocyanides as the imine source. This method allows the facile access of alkyl-, (hetero)aryl-, and alkynylzinc reagents to afford various α-substituted phenylacetone products under mild acidic hydrolysis, which are ubiquitous motifs in many pharmaceuticals and biologically active compounds. The diastereoselective reduction of imine can be accomplished to provide the expedient conversion of secondary benzylic halide into α-substituted phenethylamine derivatives with high atom economy.
Topics & Concepts
ChemistryImineCatalysisPalladiumArylSteric effectsAlkylNegishi couplingReagentCombinatorial chemistryOrganic chemistryHalideAryl halideCyanationCatalytic C–H Functionalization MethodsMulticomponent Synthesis of HeterocyclesChemical Synthesis and Analysis