Visible-Light-Promoted Cyanoalkylation/Cyclization Cascade Reaction to Assemble Polyheterocycles in Continuous Flow
Shan‐Shan Zhu, Ji-Kang Liu, Long‐Zhou Qin, Jian Wang, Xiu Duan, Xin Yuan, Jiang‐Kai Qiu, Kai Guo
Abstract
This study describes a visible-light-induced cascade reaction for preparing cyanoalkyl-containing polyheterocycles initiated by the photoinduced radical cascade addition of N -arylacrylamide derivatives using cyclic oxime esters as radical sources followed by cyanoalkyl-mediated cyclization. This protocol features outstanding functional group compatibility, providing a variety of desired phenanthridine derivatives in moderate to good yields. Moreover, the application of a microflow technique enhanced these reactions compared with the equivalent batch reaction, significantly reducing reaction times to 10 min.
Topics & Concepts
Cascade reactionPhenanthridineCascadeChemistryFunctional groupReaction conditionsRadical cyclizationVisible spectrumPhotochemistryCombinatorial chemistryOrganic chemistryMaterials scienceCatalysisChromatographyOptoelectronicsPolymerRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesInnovative Microfluidic and Catalytic Techniques Innovation