Harnessing selective PET and EnT catalysis by chlorophyll to synthesize N-alkylated quinoline-2(1H)-ones, isoquinoline-1(2H)-ones and 1,2,4-trioxanes

Abstract

Photocatalytic syntheses of quinoline-2(1H)-ones, isoquinoline-1(2H)-ones and 1,2,4-trioxanes were achieved by selective photo-induced electron transfer (PET) and energy transfer (EnT), respectively, by chlorophyll under visible light irradiation. Quinoline-2(1H)-ones, isoquinoline-1(2H)-ones and 1,2,4-trioxanes are biologically potent scaffolds and their syntheses following mild reaction protocols are highly sought after. This work showcases the divergent photocatalytic roles of chlorophyll viz., electron transfer in the case of quinolines or isoquinolines and energy transfer with allyl alcohols as substrates, affording their aerobic oxidation under green reaction conditions. The mechanistic investigations affirm that the catalytic cycle follows the electron-transfer pathway in carrying out the oxidation of N-alkyl(iso)quinolinium salts. Furthermore, the method provides an environmentally benign, simple reaction strategy for organic transformations of (N)-heterocycles.