Visible-Light-Mediated Solvent-Switched Photosensitizer-Free Synthesis of Polyfunctionalized Quinolines and Pyridines
Hirendra Nath Dhara, Amitava Rakshit, Tipu Alam, Ashish Kumar Sahoo, Bhisma K. Patel
Abstract
A solvent (2,2,2-trifluoroethanol (TFE) vs ethyl alcohol (EtOH)) switched synthesis of quinolines and pyridines is illustrated from ( E )-2-(1,3-diphenylallylidene)malononitriles via a Pd(II)-catalyzed photochemical process. The active catalyst [L 2 Pd(0)] generated serves as an exogenous photosensitizer. The process offers predominantly Z -alkenylated quinolines and pyridines in TFE and EtOH, respectively. Furthermore, large-scale synthesis and a few interesting post-synthetic modifications have been demonstrated.
Topics & Concepts
ChemistryPhotosensitizerCatalysisSolventCombinatorial chemistryAlcoholPhotochemistryEthanolOrganic chemistryCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques