2021/10/27
Keio University
A research group led by Associate Professor Takuya Kochi of the Department of Chemistry, Faculty of Science and Technology, Keio University, has successfully developed a new method for constructing the cyclic structure of organic molecules while simultaneously forming two carbon-boron bonds at remote positions. So-called "domino" reactions, which create multiple bonds within an organic molecule continuously and in a single step, have been widely used as a highly efficient method for creating complex organic molecules, but they have been limited to cases where the formed bonds are located in close proximity within the product. In 2019, this research group pioneered the world's first "domino marble-type" reaction, which continuously constructs bonds at "remote positions." More recently, "remote difunctionalization" reactions that form two bonds at distant positions have been developed by many researchers. However, there has been no method for forming three or more bonds that are remote from each other. In this study, by using a compound called diboron, which has a boron-boron bond, as a reagent, the researchers have achieved a novel molecular transformation reaction that constructs a cyclic structure, introduces two boron moieties onto the organic molecule, and continuously forms three bonds remote from each other. The cyclic compounds obtained by this method, which possess useful carbon-boron bonds for organic synthesis at unique positions, can be further converted into a variety of organic molecules. The development of this method is expected to advance "remote functionalization" reactions, which have recently attracted attention as an innovative organic synthesis method, to a new stage and lead to further breakthroughs in organic synthetic chemistry.
The results of this research were published online in the "Journal of the American Chemical Society" on October 25, 2021 (local time).
For the full press release, please see below.