Photoinduced EDA Complexes Enabled Radical Tandem Cyclization/Arylation of Unactivated Alkene with 2-Amino-1,4-naphthoquinones
Bin Sun, Xiayue Shi, Xiaohui Zhuang, Panyi Huang, Rongcheng Shi, Rui Zhu, Can Jin
Abstract
A visible-light-induced radical tandem cyclization/arylation between 2-amino-1, 4-naphthoquinone and N-allyl-2-bromo-2,2-difluoroacetamides has been developed without an external photocatalyst. The transformation could be carried out at room temperature and gave a variety of C-3-functionalized 2-amino-1,4-naphthoquinone derivatives in moderate to excellent yields. Moreover, mechanistic studies revealed that the reaction is driven by the formation of an electron donor–acceptor (EDA) complex.
Topics & Concepts
ChemistryTandemAlkeneRadical cyclizationPhotochemistryAcceptorNaphthoquinoneCombinatorial chemistryMedicinal chemistryOrganic chemistryCatalysisCondensed matter physicsMaterials sciencePhysicsComposite materialRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsFluorine in Organic Chemistry