Preparation of Trifluoromethylated Compounds via Anodic Oxidation of 4,4,4-Trifluoro-3,3-dimethoxybutyric Acid

Abstract

The Kolbe electrolysis of 4,4,4-trifluoro-3,3-dimethoxybutyric acid (TDBA) gave corresponding homo-coupling product, 1,1,1,6,6,6-hexafluoro-2,2,4,4-tetramethoxyhexane, which could be converted to the diene by treating with TiCl4 followed by dehydrochlorination. Furthermore, the crossed Kolbe product from TDBA and 3-hydroxy-2-trifluoromethylpropionic acid was converted to tetrahydrofurans and an 1-olefine.

Kolbe Carbon−Carbon Coupling Electrosynthesis Using Solid-Supported Bases

“…The yield of 2 was calculated by means of 19 F NMR by using a known amount of monofluorobenzene (96 mg, 1 mmol) as an internal standard. The product 2 was identified by comparison with the literature values using 1 H and 19 F NMR and mass spectroscopy.…”

“…Next, we investigated Kolbe electrolysis of 1 as a model reaction using solid-supported bases. It is well-known that the uses of a platinum anode and high current density conditions are favored for Kolbe electrolysis, because they lead to a high concentration of radicals at the platinum anode surface to afford homocoupling products preferentially .…”