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. 2013 Oct 25;52(44):11628-31.
doi: 10.1002/anie.201306094. Epub 2013 Sep 5.

Rapid and efficient trifluoromethylation of aromatic and heteroaromatic compounds using potassium trifluoroacetate enabled by a flow system

Mao Chen  1 , Stephen L Buchwald
Affiliations

Rapid and efficient trifluoromethylation of aromatic and heteroaromatic compounds using potassium trifluoroacetate enabled by a flow system

Mao Chen et al. Angew Chem Int Ed Engl. .

Abstract

Going to the source: The trifluoromethylation of aryl/heteroaryl iodides has been demonstrated using a flow system, thus enabling a rapid rate of reaction. A broad spectrum of trifluoromethylated compounds was prepared in good to excellent yields using CF3 CO2 K as the trifluoromethyl source. The process has the advantage of short reaction times and uses convenient [CF3 ] sources.

Keywords: copper; cross-coupling; flow chemistry; fluorine; synthetic methods.

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Figures

Figure 1
Figure 1
Flow setup for the aromatic trifluoromethylation. See the Supporting Information for details.
Figure 2
Figure 2
Hammett plots of competition experiments. See the Supporting Information for details.
Scheme 1
Scheme 1
Aromatic trifluoromethylation under batch and flow conditions.
Scheme 2
Scheme 2
Trifluoromethylation of ethyl 4-iodobenzoate on 10 mmol scale. See the Supporting Information for details.
See this image and copyright information in PMC

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