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Transition-metal free selective C(α)–C(β) bond cleavage of trifluoromethyl ketones with amidines under air: facile access to 5-trifluoromethylated Imidazol-4-ones

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Abstract

A novel and efficient strategy for the transformation of trifluoromethyl ketones is reported. The selective C(α)–C(β) bond cleavage of trifluoromethyl ketones is realized with amidines under air. This transition-metal free reaction system employs green molecular oxygen as an oxidant as well as an O-source, delivering various useful 5-trifluoromethylated imidazol-4-ones in high yields. Preliminary mechanism studies indicate that this reaction proceeds through a 1,2-aryl migration pathway rather than a radical mechanism.

Graphical abstract: Transition-metal free selective C(α)–C(β) bond cleavage of trifluoromethyl ketones with amidines under air: facile access to 5-trifluoromethylated Imidazol-4-ones

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Publication details

The article was received on 08 Jan 2019, accepted on 08 Feb 2019 and first published on 12 Feb 2019


Article type: Research Article
DOI: 10.1039/C9QO00029A
Citation: Org. Chem. Front., 2019, Advance Article

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    Transition-metal free selective C(α)–C(β) bond cleavage of trifluoromethyl ketones with amidines under air: facile access to 5-trifluoromethylated Imidazol-4-ones

    C. Zhu, C. Liu, H. Zeng, F. Chen and H. Jiang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO00029A

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