Prof. Kwangmin Shin (Deparment of Chemistry) Develops 

New Carbon-Oxygen Bond Formation Reaction Applicable to Pharmaceutical Synthesis

▲ Prof. Kwangmin Shin (left), Prof. Hyunwoo Kim of POSTECH (right)

Professor Kwangmin Shin’s research team (Department of Chemistry) developed a new carbon-oxygen bond formation reaction that combines electrochemical oxidation into a cobalt catalyst system through collaboration with professor Hyunwoo Kim of POSTECH. Using this, the research team said that tertiary substituted alkyl aryl ethers, which have been very difficult to synthesize so far, can be efficiently synthesized from phenol and olefin, which are cheap materials.

Alkyl aryl ether is a very important structure in pharmaceutical synthesis and developing a method for efficiently synthesizing it has been a very important topic in the field of organic chemistry. Although a carbon-oxygen bond formation reaction through hydroetherification between phenol and olefin has been proposed as an efficient method of synthesizing this, there is a limit to its application to complex pharmaceutical synthesis.

To solve this problem, the joint research team developed a new hydroetherification reaction that applies an electrochemical oxidation method to a cobalt catalyst system to efficiently generate a carbon cation intermediate, a high-energy intermediate, from an olefin starting material, and then undergo an efficient carbon-oxygen bond formation reaction with phenol.

The research team succeeded in synthesizing tertiary substituted alkyl aryl ethers, which were very difficult with the previously developed synthesis method, using the developed technology, and confirmed that it can be applied to the synthesis of pharmaceutical and drug active substance derivatives.

Prof. Shin and Prof. Kim said, “This study is significant in developing a novel organic synthesis method that can be applied to the synthesis of tertiary substituted aryl alkyl ethers, which was very difficult with the existing methods, and is expected to be practically utilized in the synthesis of pharmaceuticals in the future.”

This study was conducted with the support of the Korea Research Foundation’s New Research Project and Basic Laboratory Project, and was published on Sep. 2 in the ACS Catalysis Journal (IF: 13.7), a world-class academic journal in the field of catalyst chemistry.

* Paper name: Electrocatalytic Radical-Polar Crossover Hydroetherification of Alkenes with Phenols

* DOI: https://doi.org/10.1021/acscatal.2c02436)