Organocations such as trityl cation effectively promote a variety of organic reactions. The electrochemically generated carbocations [1] can also be utilized for the efficient promoter of these reactions and are applicable to a redox-switchable system which involving entirely organic compounds. The transformation using a redox-switchable catalyst is an emerging research field that seeks to regulate chemical reactions by the simple reduction-oxidation manipulation. For example, when the solution of an aldehyde, enol silyl ether and a precursor of organo-dication were subjected to the electrochemical oxidation, the aldol reaction smoothly started. Subsequent electrochemical reduction of the solution brought the reaction to a stop. We would demonstrate the utility and applicability of the present investigation. Some preliminary applications to the electrochemical microflow system will also be discussed.

[1] M. Okajima, S. Suga, K. Itami, J. Yoshida, J. Am. Chem. Soc. 2005, 127, 6930.