Photoinduced Chloroamination Cyclization Cascade with <i>N</i>-Chlorosuccinimide: From <i>N</i>-(Allenyl)sulfonylamides to 2-(1-Chlorovinyl)pyrrolidines
Emanuele Azzi, Giovanni Ghigo, Lorenzo Sarasino, Stefano Parisotto, Riccardo Moro, Polyssena Renzi, Annamaria Deagostino
Abstract
-chloroallene. The NCR formation triggers an intramolecular cyclization to a highly reactive pyrrolidine vinyl radical, which upon chlorination delivers the final product. Thus, NCS plays a dual role, serving both as an activator of the sulfonamido functionality and as the chlorinating agent.
Topics & Concepts
AlleneChemistryPyrrolidinePhotodissociationDeprotonationPhotochemistryMedicinal chemistryIntramolecular forceAlkeneCatalysisReactive intermediateRadical cyclizationStereochemistryOrganic chemistryIonSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions