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Upstream product

• 407-25-0 trifluoroacetic anhydride 
• 577-16-2 2-Methylacetophenone 
• 2926-29-6 Langlois reagent 
• 101640-66-8 1-(2-methylphenyl)ethenyl acetate 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 611-15-4 1-methyl-2-vinyl-benzene 

Relevant academic research and scientific papers

Direct Photoassisted α-Trifluoromethylation of Aromatic Ketones with Trifluoroacetic Anhydride (TFAA)

Direct α-Trifluoromethylation of acetophenone derivatives was achieved by using trifluoroacetic anhydride (TFAA) as the trifluoromethyl source and pyridine-N-oxide (Py?O) as activator and oxidant under visible light irradiation and tris-(2,2′-bipyridine)ruthenium(II) hexafluorophosphate (Ru(bpy)3(PF6)2) as the photocatalyst. Different acetophenone derivatives could be converted to the corresponding α-CF3 derivatives with high selectivity. Extensive mechanistic investigation revealed the formation of vinyl trifluoroacetate as the key intermediate for this transformation. (Figure presented.).

Photooxidative Keto-Trifluoromethylation of Styrenes by Means of an Anthraquinone-Based Organocatalyst

α-Trifluoromethyl ketones are versatile building blocks for the synthesis of various trifluoromethyl-functionalized molecules. Although there are significant advantages in the development of methods toward direct transformations of styrenes into α-trifluoromethyl ketones, most procedures leading to α-trifluoromethyl ketones require heavy- or transition-metal-based complexes. Herein, a novel method is developed for the synthesis of α-trifluoromethyl ketones via anthraquinone-catalyzed photooxidative keto-trifluoromethylation of styrenes with the readily available Langlois reagent (CF 3 SO 2 Na) under an oxygen atmosphere. The reactions proceed smoothly to give the products in moderate to excellent yield with good selectivity.

Continuous flow α-trifluoromethylation of ketones by metal-free visible light photoredox catalysis

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

Highly efficient Cu(I)-catalyzed trifluoromethylation of aryl(heteroaryl) enol acetates with CF3 radicals derived from CF3SO 2Na and TBHP at room temperature

An efficient method for the Cu(I)-catalyzed synthesis of α-trifluoromethyl ketones via the addition of CF3 to aryl(heteroaryl) enol acetates by using the readily available CF 3SO2Na (Langlois reagent) has been developed. The reaction is experimentally simple and carried out at room temperature, providing good to excellent yields with wide functional group tolerance.

PhI(OAc)2-mediated radical trifluoromethylation of vinyl azides with Me3SiCF3

The fluorine-containing organic motif is becoming privileged in pharmaceuticals, agrochemicals, and functional materials, owing to its unique properties such as electron-withdrawing character, metabolic stability, and lipophilicity. Described herein is the PhI(OAc)2-mediated radical trifluoromethylation of vinyl azides with Me3SiCF3 to efficiently generate α-trifluoromethyl azines. The resulting α-trifluoromethyl azines were successfully transformed to valuable fluorine-containing molecules such as α-trifluoromethyl ketones, β-trifluoromethyl amines, 5-fluoropyrazoles, and trifluoroethyl isoquinolines. Trifluoromethylated diversity: The title reaction (see scheme) efficiently leads to α-trifluoromethyl azines, which were successfully transformed into valuable fluorine-containing molecules such as α-trifluoromethyl ketones, β-trifluoromethyl amines, 5-fluoropyrazoles, and trifluoroethyl isoquinolines. Copyright

Oxidative trifluoromethylation of unactivated olefins: An efficient and practical synthesis of α-trifluoromethyl-substituted ketones

An economical approach to α-CF3-substituted ketones, which are important intermediates in synthetic and medicinal chemistry, employs olefins and the readily available Langlois reagent (CF3SO 2Na). The reaction is operationally simple, proceeds at room temperature, and exhibits an excellent tolerance toward a wide variety of functional groups. Copyright