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Acyl Radicals from α-Keto Acids: Metal-Free Visible-Light-Promoted Acylation of Heterocycles

Hu-Lin Zhu, Fan‐Lin Zeng, Xiaolan Chen, Kai Sun, Hao‐Cong Li, Xiaoya Yuan, Lingbo Qu, Bing Yu

2021Organic Letters155 citationsDOI

Abstract

A general and metal-free visible-light-induced decarboxylative arylation procedure at room temperature was described for the construction of acylated heterocyclic derivatives, such as benzimidazo/indolo[2,1-a]isoquinolin-6(5H)-ones, aroylazaspiro[4.5]trienones, thioflavones, and so on. This practical arylation procedure was conducted by using 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile (4CzIPN) as a photocatalyst under mild conditions, which avoided the use of an additional base, traditional heating, and metal reagents.

Topics & Concepts

ChemistryAcylationReagentRadicalTetraMetalBase (topology)Free baseCombinatorial chemistryVisible spectrumPhotocatalysisOrganic chemistryPhotochemistryMedicinal chemistryCatalysisSalt (chemistry)OptoelectronicsPhysicsMathematical analysisMathematicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsSulfur-Based Synthesis Techniques