Reinventing Benzyne Chemistry via Intramolecularity
Wednesday 23 October 2024, 05:00pm
Dr. Hiroshi Takikawa, Kyoto University, Japan
Location : AB2-5A
Abstract: Silicon tethers have long been recognized in organic synthesis as easily installable and removable auxiliaries for various intramolecular transformations. The advantages of intramolecular reactions over their intermolecular variants are high reaction efficiency, regioselectivity, and stereoselectivity. Most importantly, unique reactions that do not proceed in an intermolecular manner can be realized by setting a suitable spatial relationship between the reactants. Over the past few years, we have developed and employed silicon tethers for intramolecular reactions of benzyne, a powerful tool for introducing functionalized aromatic rings into target molecules. Our strategy has empowered various unique intramolecular reactions, i.e., regio- and peri-selective (4+2) cycloadditions with dienes, dearomative (4+2) cycloaddition with phenolates, (3+2) cycloaddition with ynamides, and ene reactions with propargylamines. Finally, we will showcase the application of this methodology in the synthesis of complex natural products.
Biosketch: Hiroshi Takikawa was born in Hiroshima, Japan (1980). He obtained his B.Eng. (2003) at Nagoya University. He received M.Sc. (2005) and D.Sc. (2008) at Tokyo Institute of Technology under the supervision of Prof. Keisuke Suzuki. After working as a postdoctoral fellow at the Max Planck Institute for Coal Research with Prof. Alois Fürstner (2008–2009), he became an assistant professor at Tokyo Institute of Technology (2009–2017). In 2017, he moved to Kyoto University as a senior lecturer and was promoted to associate professor in 2023. His current research interests are (1) natural product synthesis, (2) synthetic methods based on highly reactive species, and (3) the development of novel CPL (circularly polarized luminescence) molecules.