Manganese(III)-Mediated Selective Cascade Phosphorylation-Cyclization of Tertiary Enamides for the Synthesis of Multi-Substituted 3-Phosphorylpyridines
Xin‐Ming Xu, Sen Chen, Qian Liu, Xinyue Cao, Zhongyuan Zhao, Jinchun Chen, Yuhang Yao, Chan Yang, Kai Sun
Abstract
A novel regioselective manganese(III)-mediated radical cascade cyclization of N-propargyl enamides with various H-phosphine oxides, H-phosphinates and H-phosphonates was developed. Mechanistic studies show that the reaction is mainly composed of the selective addition of phosphonyl radical to C≡C bond and the intramolecular 6- endo -trig cyclization of vinyl radical. Utilizing this protocol, we successfully synthesized a diverse range of 3-phosphorylpyridines in high efficiency with good functional group compatibility and simple operation.
Topics & Concepts
PropargylManganeseChemistryRadical cyclizationRegioselectivityPhosphineCascadeCompatibility (geochemistry)Intramolecular forceFunctional groupCascade reactionCombinatorial chemistryMedicinal chemistryStereochemistryOrganic chemistryCatalysisMaterials scienceChromatographyPolymerComposite materialSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsAdvanced Synthetic Organic Chemistry