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Controlled chemoselective defluorination and non-defluorination for [5 + 1] aromatic annulation via Meisenheimer-type nitrogen anion and radical intermediates

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Abstract

Reported is a unique chemoselectivity approach to base-promoted defluorinative and Cu(I)-catalyzed aerobic oxidative non-defluorinative [5 + 1] condensation aromatizations of simple unsaturated ketones with ammonium salts via Meisenheimer-type nitrogen anion and radical intermediates. The CuBr/O2 catalysis provides a straightforward approach to diverse 3-fluoropyridines in high yields. The synthetic utility of the strategy is highlighted by the concise synthesis of several F-modified bioactive compounds.

Graphical abstract: Controlled chemoselective defluorination and non-defluorination for [5 + 1] aromatic annulation via Meisenheimer-type nitrogen anion and radical intermediates

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Publication details

The article was received on 01 Jul 2019, accepted on 05 Aug 2019 and first published on 07 Aug 2019


Article type: Edge Article
DOI: 10.1039/C9SC03216A
Chem. Sci., 2019, Advance Article
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    All publication charges for this article have been paid for by the Royal Society of Chemistry

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    Controlled chemoselective defluorination and non-defluorination for [5 + 1] aromatic annulation via Meisenheimer-type nitrogen anion and radical intermediates

    J. Qian, J. Zhang, H. Yang, L. Kang and G. Jiang, Chem. Sci., 2019, Advance Article , DOI: 10.1039/C9SC03216A

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