Radical-Mediated Cascade Spirocyclization of <i>N</i>-Benzylacrylamides with Polyhaloalkanes: Access to Polyhalo-Substituted Azaspirocyclohexadienones
Chuan‐Chong Peng, Fang Long, Yunchu Hu, Zhengrui Zhou, Kai‐Yi Zhang, Ru Wang, Meng‐Hua Ye, Hongbo Xiao, Li‐Jun Wu
Abstract
A novel and mild metal-free catalyzed radical-mediated cascade spirocyclization of N-benzylacrylamides with polyhaloalkanes is proposed for the preparation of polyhalo-substituted azaspirocyclohexadienones. Notably, polyhaloalkanes are employed as efficient alkyl radical sources via the cleavage of C(sp3)–H bonds. This protocol undergoes a cascade radical addition and intramolecular cyclization/dearomatization process, and enables the easy construction of multiple chemical bonds and a spiro ring in a single reaction.
Topics & Concepts
CascadeIntramolecular forceChemistryCleavage (geology)Radical cyclizationRing (chemistry)Combinatorial chemistryAlkylStereochemistryBond cleavageCatalysisMedicinal chemistryOrganic chemistryMaterials scienceFracture (geology)ChromatographyComposite materialCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques