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Issue 39, 2018
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Metal-free visible-light synthesis of quaternary α-perfluoroalkyl aldehydes via an enamine intermediate

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Abstract

Visible-light induced perfluoroalkylation of the α-position of aldehydes via enamines was developed. The reaction proceeds by electron donor–acceptor complexation of the enamine and perfluoroalkyl iodide without any additional redox catalyst. A variety of perfluoroalkyl groups are tolerated to give various quaternary α-perfluoroalkyl aldehydes. An example using proline-derived chiral amine gives high enantioselectivity.

Graphical abstract: Metal-free visible-light synthesis of quaternary α-perfluoroalkyl aldehydes via an enamine intermediate

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Publication details

The article was received on 22 Aug 2018, accepted on 18 Sep 2018 and first published on 19 Sep 2018


Article type: Communication
DOI: 10.1039/C8OB02058B
Citation: Org. Biomol. Chem., 2018,16, 7120-7123
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    Metal-free visible-light synthesis of quaternary α-perfluoroalkyl aldehydes via an enamine intermediate

    H. Matsui, M. Murase and T. Yajima, Org. Biomol. Chem., 2018, 16, 7120
    DOI: 10.1039/C8OB02058B

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