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Article Abstract
A scalable straightforward synthesis of monofluoro- and difluoromethyl triflate CF SO OCH F (M ) and CF SO OCHF (M ) through electrochemical fluorination (ECF, Simons process) of methyl triflate M in anhydrous hydrogen fluoride at nickel anodes is presented. The ECF method is also feasible for the preparation of the deuterated analogues CF SO OCD F (M ) and CF SO OCDF (M ). Surprisingly, no H/D exchange occurs during ECF of CF SO OCD (M ); this provides further evidence for a NiF /NiF -mediated ECF mechanism. The ECF of selected partially fluorinated ethyl triflates is described, and electrochemical fluorination of CF SO OCH CF (E ) leads to the until now unknown chiral CF SO OCHFCF (E ). The analogous fluoromethyl and fluoroethyl nonaflates are also accessible by ECF. This study contains detailed spectroscopic, structural, and thermal data on (fluoro)methyl and fluoro(ethyl) triflates.
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