Monofluoroalkylation and alkylation of alcohols using non-volatile reagents

Non-volatile S-Alkyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium triflate or tetrafluoroborate salts have been used to alkylate alcohols in the presence of sodium hydride. This is a simple and efficient method for the synthesis of ethers from complex alcohols and an alternative to the usual O-alkylation methods. This method was especially important for the preparation of monofluoromethyl ethers of a wide range of alcohols. Some alkylated derivatives of the precursors of some bioactive compounds were also prepared using these reagents.

Graphical abstractS-Alkyl-S-diaryl sulfonium salts as suitable reagents for the synthesis of ethers.Download high-res image (88KB)Download full-size image