From functional materials to biologically active compounds, the role of organic synthesis has been expanding continuously. Accordingly, the power and speed of organic synthesis should be enhanced to meet future demands for synthesis of various organic molecules. Our research group focuses on the development of new reactions using unstable reactive intermediates generated by various methods including electron transfer reactions and organometallic reactions to enhance the power and speed of organic synthesis of functional materials.

Unstable reactive intermediates

Organic cations have been widely used in organic synthesis as intermediates, but they are usually unstable, and therefore, should be generated in the presence of nucleophiles. We developed the “cation pool” method that involves generation and accumulation of unstable organic cations in the absence of nucleophiles by low temperature electrolysis followed by a subsequent reaction with a nucleophile. Based on the “cation pool” method we have developed new transformations such as integration of electrochemical oxidation and a radical reaction and that of electrochemical oxidation and chemical oxidation.


Flow microreactor synthesis

Flow microreactors enable conducting extremely fast reactions that are complete within seconds or less. We named such chemistry “flash chemistry” and successfully applied it to not only integration of cationic reactions but also integration of anionic reactions such as organolithium species.
In general, organolithium species react with electrophilic functional groups such as carbonyl groups very rapidly, and therefore such groups should be protected prior to an organolithium reaction, if they are not involved in the desired transformation. If organolithium chemistry could be free from such a limitation, its power would be greatly enhanced. We showed that a flow microreactor enables such protecting-group-free organolithium reactions by greatly reducing the residence time.



Functional materials

Organic rechargeable batteries have received significant research interest from the viewpoints of structural diversity and sustainability of electrode materials. We showed that the Li-ion battery composed of pyrene-4,5,9,10-tetraone (PYT), which has two six-membered cyclic 1,2-diketone units, bound to polymethacrylate exhibits remarkable charge−discharge properties with a high specific capacity, excellent rechargeability, and charge−discharge ability.


添付ファイル: filePPYT.png 276件 [詳細] fileintegration.png 299件 [詳細] filemicroreactor.png 404件 [詳細]

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