Cobalt-Catalyzed C–H Activation/Annulation of Benzamides with Fluorine-Containing Alkynes: A Route to 3- and 4-Fluoroalkylated Isoquinolinones
Tatsuya Kumon, Jianyan Wu, Miroku Shimada, Shigeyuki Yamada, Tomohiro Agou, Hiroki Fukumoto, Toshio Kubota, Gerald B. Hammond, Tsutomu Konno
Abstract
The C–H activation/annulation reaction of various benzamides with fluoroalkylated alkynes in the presence of a Co(acac)2·2H2O catalyst proceeded very smoothly to give the corresponding 3- and 4-fluoroalkylated isoquinolinones in excellent yields with approximately 70% regioselectivities. These regioisomers could be successfully separated and obtained in pure form. Major or minor regioisomers were determined as 4- or 3-fluoroalkylated isoquinolinones, respectively, based on X-ray crystallographic analyses.
Topics & Concepts
ChemistryAnnulationStructural isomerCatalysisRegioselectivityMedicinal chemistryStereochemistryOrganic chemistryCatalytic C–H Functionalization MethodsFluorine in Organic ChemistryCyclopropane Reaction Mechanisms