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Updated: Feb 22, 2026

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
Published on: January 19, 2016
Aminofluorination: transition-metal-free N-F bond insertion into diazocarbonyl compounds
Gui Chen1, Jinshuai Song2, Yinghua Yu1
1Key Laboratory of Coal to Ethylene Glycol and Its Related Technology , Fujian Institute of Research on the Structure of Matter , Chinese Academy of Sciences , Yangqiao west road 155# , Fuzhou , Fujian 350002 , China . Email: huangxl@fjirsm.ac.cn ; http://www.fjirsm.cas.cn/yjxt/yyhxyjzs/hxlktz/.
Abstract:
Gem-aminofluorination of diazocarbonyl compounds has been achieved for the first time. This reaction proceeds under mild conditions and does not require any transition-metal promoter or catalyst. Treatment of diazoesters with N-fluorobenzenesulfonimide (NFSI), which serves as both a fluorine and nitrogen source, results in the facile construction of C-N and C-F bonds, providing aminofluorination products in moderate to excellent yields. Kinetic studies and DFT calculations have provided valuable insight into the potential mechanism for this novel N-F bond insertion.
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