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Issue 3, 2016
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Aminofluorination: transition-metal-free N–F bond insertion into diazocarbonyl compounds

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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.

Graphical abstract: Aminofluorination: transition-metal-free N–F bond insertion into diazocarbonyl compounds

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Publication details

The article was received on 07 Nov 2015, accepted on 14 Dec 2015 and first published on 14 Dec 2015


Article type: Edge Article
DOI: 10.1039/C5SC04237B
Chem. Sci., 2016,7, 1786-1790
  • Open access: Creative Commons BY license
    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Aminofluorination: transition-metal-free N–F bond insertion into diazocarbonyl compounds

    G. Chen, J. Song, Y. Yu, X. Luo, C. Li and X. Huang, Chem. Sci., 2016, 7, 1786
    DOI: 10.1039/C5SC04237B

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