Construction of C–P Bonds from Free Cyclobutanone Oximes and Chlorophosphines via Radical–Radical Coupling
Lulu Yang, Jiale Wu, Yang Li, Yuhai Tang, Jing Li, Silong Xu
Abstract
Herein, we report a catalyst-free reaction of cyclobutanone oximes with chlorophosphines (R 2 PCl), which forms a fragile C═N–O–PR 2 species that undergoes N–O homolysis, fragmentation, and radical–radical coupling, leading to the formation of cyano-containing phosphine oxides in good yields. The reaction features an in situ activation of cyclobutanone oximes for radical generation, in which R 2 PCl plays a dual role as both an activator and a reactant.
Topics & Concepts
CyclobutanoneChemistryHomolysisPhotochemistryRadicalCatalysisFragmentation (computing)Coupling reactionRadical cyclizationMedicinal chemistryPhosphineOrganic chemistryRing (chemistry)Computer scienceOperating systemSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization MethodsRadical Photochemical Reactions