Visible-Light-Induced Photoaddition of <i>N</i>-Nitrosoalkylamines to Alkenes: One-Pot Tandem Approach to 1,2-Diamination of Alkenes from Secondary Amines
Dilip V. Patil, Tengda Si, Hun Young Kim, Kyungsoo Oh
Abstract
The generation of aminium radical cation species from N-nitrosoamines is disclosed for the first time through visible-light excitation at 453 nm. The developed visible-light-promoted photoaddition reaction of N-nitrosoamines to alkenes was combined with the o-NQ-catalyzed aerobic oxidation protocol of amines to telescope the direct handling of harmful N-nitroso compounds, where the desired α-amino oxime derivatives were obtained in a one-pot tandem N-nitrosation and photoaddition sequence.
Topics & Concepts
ChemistryTandemOximePhotochemistryCascade reactionAminationVisible spectrumCombinatorial chemistryMedicinal chemistryCatalysisOrganic chemistryMaterials scienceOptoelectronicsComposite materialPhysicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods