Issue 39, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
22 Aug 2018
Accepted
18 Sep 2018
First published
19 Sep 2018

Org. Biomol. Chem., 2018,16, 7120-7123

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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