Palladium-Catalyzed Cascade Carbonylative Synthesis of Perfluoroalkyl and Carbonyl-Containing 3,4-Dihydroquinolin-2(1<i>H</i>)-one Derivatives
Shangyuan Wang, Jiangjie Zhang, Jian‐Shu Wang, Jun Ying, Xiao‐Feng Wu
Abstract
A palladium-catalyzed cascade radical cyclization and carbonylation of 1,7-enynes with perfluoroalkyl iodides and alcohols has been described. This procedure provides a facile and efficient approach for the construction of 3,4-dihydroquinolin-2(1H)-one skeletons by using benzene-1,3,5-triyl triformate (TFBen) as the CO source. This method enables the incorporation of both perfluoroalkyl and carbonyl units into the 3,4-dihydroquinolin-2(1H)-one skeletons, producing a variety of 3,4-dihydroquinolin-2(1H)-one derivatives in moderate to high yields and with excellent E/Z selectivity.
Topics & Concepts
CarbonylationChemistryPalladiumCatalysisBenzeneSelectivityCombinatorial chemistryCascadeOrganic chemistryCarbon monoxideChromatographyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsFluorine in Organic Chemistry