Synthesis of α‐ and β‐Carbolines by a Metalation/Negishi Cross‐Coupling/S <sub>N</sub> Ar Reaction Sequence
Shainthavaan Sathiyalingam, Stefan Roesner
Abstract
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
Topics & Concepts
Negishi couplingChemistryIntramolecular forceMetalationSequence (biology)Combinatorial chemistryNucleophilic aromatic substitutionCoupling (piping)NucleophileNucleophilic substitutionCoupling reactionFlow chemistryStereochemistryOrganic chemistryCatalysisMechanical engineeringBiochemistryEngineeringSynthesis and bioactivity of alkaloidsCoordination Chemistry and OrganometallicsSynthesis and pharmacology of benzodiazepine derivatives