Competition between electroauxiliaries. Selective electrochemical oxidation of heteroatom compounds having silicon and tin on the same carbon

The selective electrochemical oxidation of heteroatom compounds having two different types of electroauxiliaries, i.e. silicon and tin on the same α carbon has been achieved. The C-Sn bond was cleaved selectively and a nucleophile was introduced. The second oxidation of the compound thus obtained gave rise to the cleavage of the C-Si bond and the introduction of a second nucleophile. The present study indicates the feasibility of the redox potential based strategies using electroauxiliaries.