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Transition metal-free aminofluorination of β,γ-unsaturated hydrazones: base-controlled regioselective synthesis of fluorinated dihydropyrazole and tetrahydropyridazine derivatives

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Abstract

Various base-controlled regioselective reactions of β,γ-unsaturated hydrazones with Selectfluor were achieved under transition metal-free conditions. In the presence of K2HPO4 or NaHCO3, the intramolecular aminofluorination reaction took place readily to give the corresponding monofluoromethylated dihydropyrazoles or fluoro-tetrahydropyridazines, respectively. The possible pathways were proposed based on the experimental results.

Graphical abstract: Transition metal-free aminofluorination of β,γ-unsaturated hydrazones: base-controlled regioselective synthesis of fluorinated dihydropyrazole and tetrahydropyridazine derivatives

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Publication details

The article was received on 08 Dec 2017, accepted on 25 Jan 2018 and first published on 26 Jan 2018


Article type: Research Article
DOI: 10.1039/C7QO01105A
Citation: Org. Chem. Front., 2018, Advance Article
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    Transition metal-free aminofluorination of β,γ-unsaturated hydrazones: base-controlled regioselective synthesis of fluorinated dihydropyrazole and tetrahydropyridazine derivatives

    J. Zhao, M. Jiang and J. Liu, Org. Chem. Front., 2018, Advance Article , DOI: 10.1039/C7QO01105A

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