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CF<sub>3</sub>SO<sub>2</sub>Na-Mediated Visible-Light-Induced Cross-Dehydrogenative Coupling of Heteroarenes with Aliphatic C(sp<sup>3</sup>)–H Bonds

Cuilian Zeng, Hao Wang, Di Gao, Zhen Zhang, Dong Ji, Wei He, Chengkou Liu, Zhao Yang, Zheng Fang, Kai Guo

2022Organic Letters30 citationsDOI

Abstract

Minisci-type reaction is one of the important means to construct C(sp3)–H functionalization of heteroarenes. According to traditional methods, stoichiometric amounts of precious transition metal catalysts and chemical oxidants were required at high temperatures. Here, a green and gentle novel Minisci-type method was developed via visible-light-induced cross-dehydrogenative coupling of heteroarenes with aliphatic C(sp3)–H bonds under oxidant-free and transition-metal-catalyst-free conditions. Only the catalytic equivalent of CF3SO2Na and room temperature were required to maintain an efficient reaction.

Topics & Concepts

CatalysisStoichiometryChemistryCoupling reactionTransition metalCoupling (piping)Visible spectrumPhotochemistryReaction conditionsMetalCombinatorial chemistryOrganic chemistryMaterials scienceOptoelectronicsMetallurgyCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
CF<sub>3</sub>SO<sub>2</sub>Na-Mediated Visible-Light-Induced Cross-Dehydrogenative Coupling of Heteroarenes with Aliphatic C(sp<sup>3</sup>)–H Bonds | Litcius