Synthesis of α‐ and β‐Carbolines by a Metalation/Negishi Cross‐Coupling/SNAr Reaction Sequence

Abstract A methodology for the synthesis of α‐ and β‐carbolines from fluoropyridines and 2‐haloanilines is reported. This procedure consists of a four‐step directed ortho ‐lithiation, zincation, Negishi cross‐coupling, and intramolecular nucleophilic aromatic substitution, providing access to a diverse set of functionalized carbolines. While the procedure is applicable to batch conditions, the generation of arylzinc intermediates in continuous flow has been demonstrated. magnified image