Basic concepts of "cation pool" and "cation flow" methods and their applications in conventional and combinatorial organic synthesis.
Carbocations have been generally considered to be relatively unstable and transient species. But the "cation pool" method enables the easy accumulation of carbocations in conventional reaction media such as dichloromethane. In the "cation pool" method, carbocations are generated by low-temperature electrochemical oxidation and accumulated in a solution. In the next step, the carbocations thus produced are allowed to react with various nucleophiles. Combinatorial parallel synthesis based upon the "cation pool" method has also been developed. The applicability of the "cation pool" method depends upon the stability of the cation that is accumulated. This problem can be overcome by the "cation flow" method. In the "cation flow" method, carbocations are generated in a microflow electrochemical system. Short residence times and efficient temperature control of the microflow system are advantageous. Combinatorial sequential synthesis has been achieved based on the "cation flow" method.
Yoshida
Jun-ichi
J
Department of Synthetic Chemistry & Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 606-8501, Japan. yoshida@sbchem.kyoto-u.ac.jp
Suga
Seiji
S