Reductive Alkylation of Quinolines to <i>N</i>-Alkyl Tetrahydroquinolines Catalyzed by Arylboronic Acid
Priyanka Adhikari, Dipanjan Bhattacharyya, Sekhar Nandi, Pavan K. Kancharla, Animesh Das
Abstract
A boronic acid catalyzed one-pot tandem reduction of quinolines to tetrahydroquinolines followed by reductive alkylation by the aldehyde has been demonstrated. This step-economcial synthesis of N-alkyl tetrahydroquinolines has been achieved directly from readily available quinolines, aldehydes, and Hantzsch ester under mild reaction conditions. The mechanistic study demonstrates the unique behavior of organoboron catalysts as both Lewis acids and hydrogen-bond donors.
Topics & Concepts
ChemistryAlkylationCatalysisAlkylAldehydeLewis acids and basesOrganic chemistryCombinatorial chemistryTandemBoronic acidPrimary (astronomy)AstronomyMaterials scienceComposite materialPhysicsAsymmetric Hydrogenation and CatalysisChemical Synthesis and AnalysisOrganoboron and organosilicon chemistry