Abstract
Anodic methoxylation of various types of N-(fluoroethyl)amines, ArRNCH 2 R f (R f =CF 3 , CHF 2 , CH 2 F, etc.) has been systematically studied and it was found that a methoxy group was exclusively or preferentially introduced into the position a to the fluoromethyl (Rf) group, depending on the Rf and R groups. The effect of the R f group on the promotion of the anodic α-methoxylation decreased in the order CF 3 , CHF 2 , and CH 2 F. This remarkable promotion effect and unique regioselectivity can be explained mainly in terms of the α-CH kinetic acidities of the cation radicals formed by one-electron oxidation of the amines. The α-methoxylated products are highly useful precursors for the construction of carbon-carbon bonds α to the trifluoromethyl and difluoromethyl groups, which is difficult by other methods
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