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Application of Bifunctional 2-Amino-1,4-naphthoquinones in Visible-Light-Promoted Photocatalyst-Free Alkene Perfluoroalkyl-Alkenylation

Lin Tang, Fang Yang, Zhen Yang, Hanfei Chen, Hao Cheng, Shuaifei Zhang, Qiuju Zhou, Wei‐Hao Rao

2020Organic Letters41 citationsDOI

Abstract

A simple and practical photochemical strategy for intermolecular perfluoroalkyl-alkenylation of alkenes with 2-amino-1,4-naphthoquinones and perfluoroalkyl iodides has been demonstrated under visible-light irradiation. Mechanistic studies reveal that easily available 2-amino-1,4-naphthoquinone substrates can serve as efficient photosensitizers to activate perfluoroalkyl iodides through a photoredox process. Therefore, the developed radical relay reaction proceeds smoothly without additional transition metals and photocatalysts.

Topics & Concepts

ChemistryAlkenePhotochemistryPhotocatalysisBifunctionalIntermolecular forceVisible spectrumNaphthoquinoneCombinatorial chemistryOrganic chemistryMoleculeCatalysisPhysicsOptoelectronicsFluorine in Organic ChemistryRadical Photochemical ReactionsOxidative Organic Chemistry Reactions
Application of Bifunctional 2-Amino-1,4-naphthoquinones in Visible-Light-Promoted Photocatalyst-Free Alkene Perfluoroalkyl-Alkenylation | Litcius