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Visible light-induced selective aerobic oxidative transposition of vinyl halides using a tetrahalogenoferrate(III) complex catalyst

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Abstract

We report tetrahalogenoferrate(III) complexes as a new kind of iron photocatalyst. These complexes are easily prepared from FeCl3 with lithium bromide or ammonium bromides, and have a good and tunable photo-sensitivity in the visible light region. Their distinct catalytic mode with FeCl3 enables a highly chemoselective photooxygenation of benzylic sp3 C–H, providing a series of carbonyls in moderate to excellent yields. The method has also been employed in the challenging aerobic oxidative transposition of vinyl halides, thus facilitating a mild and highly efficient approach to access significant α-halo ketones with a broad substrate scope. The disclosure of tetrahalogenoferrate(III) complex photocatalysts should provide inspiration for their expansion to new aerobic oxidative reactions and even anaerobic variations.

Graphical abstract: Visible light-induced selective aerobic oxidative transposition of vinyl halides using a tetrahalogenoferrate(iii) complex catalyst

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Publication details

The article was received on 05 Sep 2017, accepted on 10 Oct 2017 and first published on 11 Oct 2017


Article type: Research Article
DOI: 10.1039/C7QO00798A
Citation: Org. Chem. Front., 2017, Advance Article
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    Visible light-induced selective aerobic oxidative transposition of vinyl halides using a tetrahalogenoferrate(III) complex catalyst

    S. Li, B. Zhu, R. Lee, B. Qiao and Z. Jiang, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00798A

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