Visible-Light-Induced Desaturative β-Alkoxyoxalylation of N-Aryl Cyclic Amines with Difluoromethyl Bromides and H<sub>2</sub>O Via a Triple Cleavage Process
Bin Sun, Peixuan Li, Yu Jiang, Lulu Yang, Panyi Huang, Runpu Shen, Mao-Jie Chen, Jiayang Wang, Can Jin
Abstract
A visible-light-driven desaturative β-alkoxyoxalyation of N-aryl cyclic amines with difluoromethyl bromides and H 2 O has been reported. This tandem reaction is triggered by homolysis of the C–Br bond to produce the difuoroalkyl radical, which undergoes the subsequent defluorinated β-alkoxyoxalylation cascades to afford a wide range of β-ketoester/ketoamides substituted enamines. The prominent feature of this reaction contains photocatalyst-free, transition-metal free, and mild conditions. The 18 O labeling experiment disclosed that H 2 O is the oxygen source of the carbonyl unit.
Topics & Concepts
ChemistryHomolysisArylTandemBond cleavageVisible spectrumMedicinal chemistryPhotochemistryRadicalReaction conditionsTriple bondCatalysisPolymer chemistryOrganic chemistryDouble bondAlkylPhysicsComposite materialMaterials scienceOptoelectronicsFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods