Visible Light-Promoted Aromatization-Driven Deconstructive Fluorination of Spiro Carbocycles
Wenpeng Yang, Hong-Jie Miao, Le Liu, Xin‐Hua Duan, Li‐Na Guo
Abstract
A visible light-promoted aromatization-driven deconstructive fluorination of spiro carbocycles is presented. A series of spiro dihydroquinazolinones reacted efficiently with NFSI under visible light irradiation to afford the 2-(4-fluoroalkyl)quinazolin-4(3 H )-ones in good yields with excellent functional group tolerance. A radical pathway involving C–C bond cleavage and F atom transfer is proposed for the reaction. In addition, the ring-opening chlorination of spiro dihydroquinazolinones with NCS was also applicable.
Topics & Concepts
AromatizationChemistryRing (chemistry)PhotochemistryVisible spectrumBond cleavageCleavage (geology)Functional groupMedicinal chemistryOrganic chemistryCatalysisPolymerFracture (geology)PhysicsOptoelectronicsGeotechnical engineeringEngineeringFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods