Electrooxidative Inter- and Intramolecular Carbon-Carbon Bond Formation Using Organothio Groups as Electroauxiliaries

The introduction of an organothio group to an alpha-carbon of ethers results in significant decrease of the oxidation potentials. Anodic oxidation of alpha-organothioethers gives rise to facile cleavage of the C-S bond and the introduction of carbon nucleophiles on the carbon. Allylsilanes, silyl enol ethers, and trimethylsilyl cyanide serve as effective carbon nucleophiles. The anodic oxidation of the alpha-organothioethers having a carbon-carbon double bond in an appropriate position using Bu(4)NBF(4) as the supporting electrolyte leads to the effective cyclization and the introduction of the fluoride to one of the formal olefinic carbon. The present study demonstrates the effectiveness of organothio groups as electroauxiliaries in electrooxidative inter- and intramolecular carbon-carbon bond formation.