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Continuous Flow α-Trifluoromethylation of Ketones by Metal-Free Visible Light Photoredox Catalysis

David Cantillo, Oscar de Frutos, Juan A. Rincón*, Carlos Mateos and C. Oliver Kappe*

*Lilly S.A., Avda. de la Industria 30, 28108 Alcobendas-Madrid, Spain; University of Graz, Heinrichstrasse 28, A-8010 Graz, Austria, Email: rincon_juan_antoniolilly.com, oliver.kappeuni-graz.at

D. Cantillo, O. D. Frutos, J. A. Rincón, C. Mateos, C. O. Kappe, Org. Lett., 2014, 16, 876-879.

DOI: 10.1021/ol403650y


Abstract

In a continuous-flow, two-step procedure for the preparation of α-CF3-substituted carbonyl compounds, carbonyl substrates were converted in situ into the corresponding silyl enol ethers, mixed with a CF3 radical source, and then irradiated with visible light using transparent tubing and a household compact fluorescent lamp. The continuous protocol uses Eosin Y as an inexpensive photoredox catalyst and requires only 20 min for both steps.

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Key Words

flow chemistry, α-trifluoromethyl carbonyl compounds


ID: J54-Y2014