1,3-Difunctionalization of β-Alkyl Nitroalkenes via Combination of Lewis Base Catalysis and Radical Oxidation
Ye Wang, Lei Zheng, Xiaodong Shi, Yunfeng Chen
Abstract
Upon treatment with a Lewis base catalyst, β-alkyl-substituted nitroalkenes could be readily converted into allylic nitro compounds. Examples of either C-1 or C-3 functionalization methods have been reported through nitro-elimination, giving alkene products. In this work, successful 1,3-difunctionalization was achieved through a synergetic Lewis base catalysis and TBHP radical oxidation, giving vinylic alkoxyamines in good to excellent yields. This work further extended the general synthetic application of β-alkyl nitroalkenes.
Topics & Concepts
ChemistryLewis acids and basesCatalysisAlkeneAllylic rearrangementAlkylNitroOrganic chemistryBase (topology)Combinatorial chemistrySurface modificationMedicinal chemistryPhysical chemistryMathematicsMathematical analysisOxidative Organic Chemistry ReactionsCatalytic C–H Functionalization MethodsChemical Synthesis and Reactions