Oxidation of primary alkyl triflates to the corresponding aldehydes via alkoxy(N-tert-butylamino)(methyl)sulfonium triflates

Various alkoxy(N-tert-butylamino)(methyl)sulfonium triflates are prepared b y selective O-alkylation of N-tert-butylmethanesulfinamide (4c) with primar y alkyl trifluoromethane sulfonates (triflates). Successive treatment of th us formed alkoxyaminosulfonium salts with DBU smoothly affords the correspo nding aldehydes in good yields. The sequential combination of the two react ions provides a new method for oxidation of primacy alkyl triflates to alde hydes, and the present study suggests the existence of alkoxysulfilimines a s intermediates of the previously-reported direct oxidation of alcohols by using N-tert-butylphenylsulfinimidoyl chloride (1a) and DBU.