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Issue 1, 2014
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Transition-metal-free, room-temperature radical azidofluorination of unactivated alkenes in aqueous solution

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Abstract

We report herein the transition-metal-free azidofluorination of unactivated alkenes. Thus, the condensation of various alkenes with TMSN3 and Selectfluor in aqueous CH3CN at RT led to the efficient and regioselective synthesis of β-fluorinated alkyl azides with excellent functional group compatibility and good stereoselectivity. A single electron transfer mechanism involving the oxidative generation of azidyl radicals is proposed.

Graphical abstract: Transition-metal-free, room-temperature radical azidofluorination of unactivated alkenes in aqueous solution

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Publication details

The article was received on 14 Nov 2013, accepted on 25 Nov 2013 and first published on 20 Dec 2013


Article type: Research Article
DOI: 10.1039/C3QO00037K
Citation: Org. Chem. Front., 2014,1, 100-104
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    Transition-metal-free, room-temperature radical azidofluorination of unactivated alkenes in aqueous solution

    Z. Li, C. Zhang, L. Zhu, C. Liu and C. Li, Org. Chem. Front., 2014, 1, 100
    DOI: 10.1039/C3QO00037K

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