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Visible-Light-Induced Copper-Catalyzed Intermolecular Three-Component Difluoroalkyl Thiocyanidation of Alkenes

Zhaoming Hu, Yanzhao Wang, Kaiji Wang, Jingjing Wu, Fanhong Wu

2023Organic Letters33 citationsDOI

Abstract

In this report, we develop a new strategy for visible-light-induced, copper-catalyzed three-component difluoroalkyl thiocyanidation of alkenes to construct a series of important difluorothiocyanate compounds. The new approach can also be applied to perfluorothiocyanate compounds, even target molecules containing drug/natural product skeletons. Mechanistic studies provide that the copper complex plays a dual role, as both the photoredox catalyst for electron transfer and the cross-coupling catalyst for C-SCN bond formation.

Topics & Concepts

ChemistryCopperCatalysisIntermolecular forceComponent (thermodynamics)MoleculeCombinatorial chemistryVisible spectrumPhotochemistryElectron transferOrganic chemistryPhysicsOptoelectronicsThermodynamicsFluorine in Organic ChemistrySulfur-Based Synthesis TechniquesRadical Photochemical Reactions