Investigations On Several Radical Fluoroalkylation/alkylation Reactions

It is well known that F is a non-biological atom.When it is introduced into an organic compound,it can greatly change the pharmacological activity and biological activity of the original compound,improve the bioavailability,and enhance the metabolic stability in the body.Methods for preparing fluorine-containing compounds,particularly by photooxidative reduction catalysis,have received increasing attention,and radical reactions by photocatalytic oxidation have been applied to more and more reactions.In view of this,I am mainly engaged in radical fluoroalkylation/alkylation reaction and organic light-promoted alkyl radical reaction research.(1)Free radical fluoroalkylation reactionIn this section,we describe the free radical trifluoro/difluoromethylation of para-quinone methides and the hydroxytrifluoromethylation of alkenes.Free radical polyfluoroalkylation of para-quinone methides was achieved under visible-light irradiation conditions using an easily handled sodium sulfinate RfSO2Na as the fluoroalkyl radical source and an organic photocatalyst Mes-Acr+.The hydroxytrifluoromethylation of alkenes is also developed with readily available CF3SO2Na as the trifluoromethyl radical source.(2)Radical alkyl reaction via organic photocatalystA novel photocatalytic protocol is herein described for the preparation of functionalized phenols via radical alkylation of para-quinone methides under transition-metal-free conditions.The reaction is external oxidant free and performed at ambient temperature upon visible light irradiation,allowing the access to various desired products in satisfactory yields.The readily available 4-alkyl-1,4-dihydropyridines serve as the effective alkyl radical precursors.