Substituent‐Guided Switch between CH Activation and Decarboxylative Cross‐Coupling during Palladium/Copper‐Catalyzed Cascade Reactions of 2‐Aminobenzoates with 2‐Haloarylaldehydes

Abstract

Cascade switch: Phenanthridines, pyrazole[4,3-c]quinolines and isocryptolepine were prepared in one step from the Pd/Cu-catalyzed reaction between potassium 2-aminobenzoates and 2-haloarylaldehydes (see scheme). Although the reactions of 2-aminobenzoates proceeded via a cascade imination/CH functionalization, the reactions of 6-nitro-2-aminobenzoates ensued via a tandem imination/decarboxylative cross-coupling.