We have successfully developed a novel electrolytic system for non-Kolbe electrolysis based on the acid−base reaction between carboxylic acids as a substrate and solid-supported bases. It was found that the acid−base reaction between carboxylic acids and solid-supported bases preferentially takes place to reduce the cell voltage in MeOH. On the basis of the electrolytic system, non-Kolbe electrolysis of various carboxylic acids was carried out to provide the corresponding methoxylated products in excellent yields.

We have developed a novel electrolytic system for Kolbe carbon-carbon coupling electrosynthesis based on the acid-base reaction between carboxylic acids as a substrate and solid-supported bases. On the basis of the electrolytic system, Kolbe electrolysis of various carboxylic acids was successfully carried out to provide the corresponding homocoupling products in moderate to excellent yields.

We have demonstrated anodic alkoxylation of lactams followed by reactions with carbon nucleophiles in a one-pot manner using 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent. In the two-step transformation, HFIP acted as a nucleophile in the presence of solid-supported bases, while it acted as an inert solvent in the absence of solidsupported bases. This enabled us to conduct anodic alkoxylation of lactams and subsequent C-C bond forming reactions without replacing the solvent.

On the basis of the concept of site isolation in electrochemical reactions, we have successfully demonstrated acceleration of the deprotonation step in anodic methoxylation of fluoroethyl phenyl sulfides using silica gel supported bases.

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