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Photocatalytic Annulation‐Carbohalogenation of 1,7‐Enynes for Atom‐Economic Synthesis of Functionalized 3,4‐Dihydronaphthalen‐1(2<i>H</i>)‐ones

Wenzhe Ji, Haonan Shi, Ping Wei, Wen‐Juan Hao, Shu‐Jiang Tu, Bo Jiang

2020Advanced Synthesis & Catalysis13 citationsDOI

Abstract

Abstract A general and efficient photocatalytic annulation‐carbohalogenation of 1,7‐enynes with a wide variety of alkyl halides was reported, which led to the atom‐economic synthesis of functionalized 3,4‐dihydronaphthalen‐1( 2H )‐ones with good yields and high stereoselectivity under the mild and oxidant‐free conditions. The reaction demonstrated remarkable compatibility regarding alkyl halides as bifunctional reagents, such as ethyl 2‐bromo‐2,2‐difluoroacetate, ethyl 2,2‐difluoro‐2‐iodoacetate, perfluorobutyl iodide, bromotrichloromethane, and diethyl 2‐bromomalonate, and enabled wide substrate scope, high functional group tolerance, and 100% atom utilization. magnified image

Topics & Concepts

ChemistryAnnulationAlkylHalideReagentIodidePhotocatalysisStereoselectivityAtom (system on chip)Substrate (aquarium)Medicinal chemistryCombinatorial chemistryOrganic chemistryCatalysisEmbedded systemOceanographyComputer scienceGeologyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques