Synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers by the reaction of dithiocarbonates with IF5-pyridine-HF

Article abstract of DOI:10.1016/j.jfluchem.2015.04.016

Trifluoromethyl ether and difluoro(methylthio)methyl ether of phenols and aliphatic alcohols were selectively synthesized from the corresponding dithiocarbonates. When IF₅-pyridine-HF was used alone in the reaction of the dithiocarbonate, the difluoro(methylthio)methyl ether was selectively formed. On the other hand, by the additional use of Et₃N-6HF with IF₅-pyridine-HF, trifluoromethyl ether was formed selectively. Various functional groups such as ester, ether, amide, and acetonide could tolerate the reaction conditions, and various functionalized difluoro(methylthio)methyl ethers and trifluoromethyl ethers were synthesized.