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Issue 17, 2018
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NFSI-participated intermolecular aminoazidation of alkene through iron catalysis

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Abstract

An iron-catalysed intermolecular vicinal aminoazidation of alkenes, using N-fluorobenzenesulfonimide (NFSI) and trimethylsilyl azide (TMSN3) as the imidating and azidating reagents, respectively, is described, which could potentially provide a valuable route toward diverse vicinal diamine derivatives of great significance in medicinal chemistry and organic synthesis. Such iron-catalysed aminative bisfunctionalization of alkenes with NFSI has not been reported yet. Comparing to previously employed copper or palladium catalysts, the iron catalyst, FeCl2, was demonstrated to be a good alternative for its comparable efficiency and broad alkene scope. Preliminary mechanistic study suggested that this iron-catalysed reaction is realized through radical processes.

Graphical abstract: NFSI-participated intermolecular aminoazidation of alkene through iron catalysis

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Publication details

The article was received on 22 Mar 2018, accepted on 11 Apr 2018 and first published on 11 Apr 2018


Article type: Communication
DOI: 10.1039/C8OB00699G
Citation: Org. Biomol. Chem., 2018,16, 3109-3113
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    NFSI-participated intermolecular aminoazidation of alkene through iron catalysis

    B. Lei, X. Wang, L. Ma, Y. Li and Z. Li, Org. Biomol. Chem., 2018, 16, 3109
    DOI: 10.1039/C8OB00699G

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