Abstract
Tetrabutylammonium decatungstate has been exploited to photoinduce the trifluoromethylation of (hetero)aromatics and electron-poor olefins. The process made use of the cheap Langlois' reagent (CF3SO2Na) and occurred under sunlight irradiation in an acetonitrile/water mixture. The trifluoromethylation of (hetero)aromatics required the use of potassium persulfate as an additive and the mono- or bis-trifluoromethylated adducts were obtained, depending on the actual reaction conditions and the chosen substrate.
Highlights
The solvent was removed under reduced pressure from the photolyzed solution and the product isolated by purification of the residue by column chromatography
Spectroscopic data of compound 4 were in accordance with the literature.S4
Spectroscopic data of compound 13 were in accordance with the literature.S10
Summary
Purification of the residue by column chromatography (petroleum ether : ethyl acetate 8:2 as the eluant) afforded 96 mg of 1,3,5-trimethoxy-2-(trifluoromethyl)benzene (4, 54% yield) as a solid. Purification of the residue by column chromatography (petroleum ether : ethyl acetate 9:1 as the eluant) afforded 180 mg of 1,3,5-trimethoxy-2,4-bis(trifluoromethyl)benzene (5, 79% yield) as a solid. Purification of the residue by column chromatography (petroleum ether : ethyl acetate 9:1 as the eluant) afforded 70 mg of 1,4-dimethoxy-2-(trifluoromethyl)benzene (6, 45% yield) as a liquid.
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