Chlorinative Cyclization of Aryl Alkynoates Using NCS and 9-Mesityl-10-methylacridinium Perchlorate Photocatalyst
Milan Pramanik, Ashis Mathuri, Sudip Sau, Monojit Das, Prasenjit Mal
Abstract
In a chlorinative cyclization, Mes-Acr-MeClO4 acted as a visible-light photocatalyst to obtain 3-chlorocoumarins from aryl alkynoates and N-chlorosuccinimide (NCS). The radical initiated reaction proceeded in a cascading manner via Cl– addition to alkynoates. Next, 5-exo-trig spirocyclization and subsequent 1,2-ester migration led to the formation of C–C and C–Cl bonds.
Topics & Concepts
ChemistryArylPhotocatalysisPerchlorateMedicinal chemistryPhotochemistryCatalysisOrganic chemistryAlkylIonRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesOxidative Organic Chemistry Reactions