Iodine-Assisted Regioselective C3-H Chalcogenation of 4-Phenyl Aminocoumarin: Access to Unusual Dual Selenylation of N-Substituted Derivatives

Abstract

A simple, efficient, metal and photocatalyst-free, eco-friendly approach for the C3-H regioselective chalcogenation of 4-phenyl aminocoumarin, as well as abnormal dual selenylation of N-substituted 4-phenyl aminocoumarin, has been developed by using diphenyl dichalcogenides and iodine as support in green solvent PEG-400 under ambient temperature and aerobic condition. Furthermore, chalcogenation of 4-phenyl amino-2-pyrone has also been accomplished in similar conditions. The proposed mechanism is based on the control experiments and suggests an ionic pathway. The reaction offers a green synthetic path with a high yield, and the methodology is crucially significant due to its operational simplicity, convenient execution, scalability, and tolerance of various functional groups.