Photoinduced Multicomponent Heteroarylation of [1.1.1]Propellane with Katritzky Pyridinium Salts
Yulin Xiao, Jianyang Dong, Yuying Wang, Huijuan Liao, Jiayi Dang, Gang Li, Dong Xue
Abstract
(Hetero)arylated bicyclo[1.1.1]pentanes (BCPs) are important for the construction of complex druglike target molecules. Herein, we developed a method for light-induced, Cs 2 CO 3 -promoted homolytic cleavage of pyridinium C–N bonds for generating alkyl radicals from amino acid-derived Katritzky salts and use of the radicals for functionalization of [1.1.1]propellane to rapidly generate (hetero)arylated BCPs. The method features excellent functional group tolerance and a broad substrate scope and can be used to functionalize structurally complex natural products.
Topics & Concepts
ChemistryPyridiniumRadicalPropellaneFunctional groupHomolysisAlkylCombinatorial chemistryBond cleavageMoleculeSubstrate (aquarium)Pyridinium CompoundsBicyclic moleculeSurface modificationPhotochemistryOrganic chemistryPolymerCatalysisOceanographyPhysical chemistryGeologyRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques