Smyrnov, VladyslavMuriel, BastianWaser, Jerome2021-07-312021-07-312021-07-312021-07-1610.1021/acs.orglett.1c01775https://infoscience.epfl.ch/handle/20.500.14299/180249WOS:000674945400030We 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.Chemistry, OrganicChemistryvinyl azidescatalyzed cyclopropenation3+2 annulationtrialkylboranesderivativeschemistryaccessstrainSynthesis of Quinolines via the Metal-free Visible-Light-Mediated Radical Azidation of Cyclopropenestext::journal::journal article::research article