Synthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenes
Vladyslav Smyrnov, Bastian Muriel, Jérôme Waser
Abstract
We report the synthesis of quinolines using cyclopropenes and an azidobenziodazolone (ABZ) hypervalent iodine reagent as an azide radical source under visible-light irradiation. Multisubstituted quinoline products were obtained in 34-81% yield. The reaction was most efficient for 3-trifluoromethylcyclopropenes, affording valuable 4-trifluoromethylquinolines. The transformation probably proceeds through the cyclization of an iminyl radical formed by the addition of the azide radical on the cyclopropene double bond, followed by ring-opening and fragmentation.
Topics & Concepts
ChemistryHypervalent moleculeReagentAzideCyclopropeneQuinolinePhotochemistryRing (chemistry)IodineYield (engineering)Visible spectrumRadicalCombinatorial chemistryMedicinal chemistryOrganic chemistryPhysicsMetallurgyOptoelectronicsMaterials scienceCyclopropane Reaction MechanismsFluorine in Organic ChemistryCatalytic C–H Functionalization Methods