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Updated: May 12, 2026

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
Transition-metal-free tunable regioselective [3+2] cycloaddition of diaryliodonium salts with 1,3-dicarbonyl
Yixi Yang1, Shaoqing Wang1, Lin Wang1
1College of Materials and Chemical Engineering, Key Laboratory of Inorganic Nonmetallic Crystalline and Energy Conversion Materials, China Three Gorges University, Yichang, Hubei 443002, P. R. China. qintao@ctgu.edu.cn.
Abstract:
A new [3+2] cycloaddition reaction of diaryliodonium salts with 1,3-dicarbonyl compounds for the synthesis of benzofuran derivatives is reported, involving the sequential selective coupling of dual electrophilic and nucleophilic reagents. The key to this reaction is the use of a novel diaryliodonium reagent, which carries both a leaving group and a strong electron-withdrawing group (EWG). Interestingly, the choice of leaving group can dictate the reaction's selectivity. Moreover, the protocol demonstrates significant robustness, flexibility, and compatibility with a broad range of functional groups.
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