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Et3B/O2-mediated radical coupling reactions of O,Te-acetal 2 were explored using diverse electrophilic double bonds. Ethyl radical derived from Et3B under air cleaved the C–Te bond of 2 to generate α-alkoxy bridgehead radical I, which reacted with cycloalkenones, cycloalkylidenemalononitriles, allyl halides, and imines at or below ambient temperature. These intermolecular reactions from O,Te-acetal...
α-Alkoxyacyl tellurides derived from d-tartaric acid were utilized for stereoselective coupling reactions with electron-deficient double bonds. Treatment of the α-alkoxyacyl tellurides with Et3B/O2 or Et3B/O2/HSi(SiMe3)3 at room temperature promoted acyl radical formation and subsequent decarbonylation to form the corresponding α-alkoxy radicals, which added to various CC and CN bonds conjugated with...
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