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

• Difluoro(methylthio)methyl ether of phenol and alcohol was synthesized.
• A stable fluorination reagent, IF5-pyridine-HF, was used for the reaction.
• Trifluoromethyl ether was also synthesized from the dithiocarbonate.
• IF5-pyridine-HF and Et3N-6HF were used for the synthesis of trifluoromethyl ether.

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.

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