<i>gem</i>-Bromonitroalkane Involved Radical 1,2-Aryl Migration of α,α-Diaryl Allyl Alcohol TMS Ether via Visible-Light Photoredox Catalysis
Shanshan Ma, Yawen Guo, Lidong Liu, Shi Lin, Xingyu Lei, Xin‐Fang Duan, Peng Jiao
Abstract
-bromonitroalkanes with α,α-diaryl allyl alcohol trimethylsilyl ethers was reported. A cascade consisting of visible-light-induced generation of an α-nitroalkyl radical and a subsequent neophyl-type rearrangement was key to realize the coupling reactions. Structurally diverse α-aryl-γ-nitro ketones, especially those bearing a nitrocyclobutyl structure, were prepared in moderate to high yields, which could be converted into spirocyclic nitrones and imines.
Topics & Concepts
ChemistryArylAlcoholEtherTrimethylsilylPhotoredox catalysisCatalysisAllyl alcoholVisible spectrumNitroCoupling reactionPhotochemistryMedicinal chemistryOrganic chemistryPhotocatalysisAlkylOptoelectronicsPhysicsRadical Photochemical ReactionsSulfur-Based Synthesis TechniquesCatalytic C–H Functionalization Methods