Fluoroalkylation of Allylic Alcohols with Concomitant (Hetero)aryl Migration: Access to Fluoroalkylated Ketones and Evaluation of Antifungal Action against <i>Magnaporthe grisea</i>
Yanhu Zhang, Ziyang Ren, Yun‐Lin Liu, Zhentao Wang, Zhaodong Li
Abstract
Fluoroalkyl(hetero)arylation of allylic alcohols with perfluoroalkyl iodide or difluoroacetic acid as fluoroalkyl source was developed herein, delivering functionalized ketones containing an α‐quaternary center. Formation of the fluoroalkyl radical was followed by its intermolecular addition to alkenes and the migration of a (hetero)aryl group with the concomitant generation of a ketone group to finish the domino sequence. Mechanistic studies indicated that the aryl migration proceeded through neophyl rearrangement in a radical pathway. Moreover, preliminary antifungal evaluation against Magnaporthe grisea is also described for the first time.
Topics & Concepts
ChemistryArylAntifungalAllylic rearrangementKetoneIodideOrganic chemistryCombinatorial chemistryMedicinal chemistryStereochemistryCatalysisAlkylMicrobiologyBiologyFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsRadical Photochemical Reactions