Visible-Light-Mediated [2+2+1] Carbocyclization Reactions of 1,7-Enynes with Bromofluoroacetate to Form Fused Monofluorinated Cyclopenta[<i>c</i>]quinolin-4-ones
Yi Qu, Wentao Xu, Jingjing Zhang, Yuxiu Liu, Yongqiang Li, Hongjian Song, Qingmin Wang
Abstract
Herein, we describe a new protocol for photoinduced radical [2+2+1] carbocyclization reactions of 1,7-enynes with bromofluoroacetate. These reactions, which proceed via a cascade involving fluoroalkylation, 6-exo-dig and 5-endo-trig cyclizations, H-transfer step, and oxidative dehydrogenation, provide an efficient and general route to a variety of fused monofluorinated cyclopenta[c]quinolin-4-one derivatives.
Topics & Concepts
ChemistryDehydrogenationCombinatorial chemistryPhotochemistryStereochemistryOrganic chemistryCatalysisFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods