120th General Meeting of the KCS

Type Symposium
Area Current Trends in Organic Chemistry III: New Reactions and Methodology
Room No. Room 304+305+306
Time FRI 15:00-:
Code ORGN3-2
Subject Development of Transient Ligands for Palladium-catalyzed sp3 C-H Bond Arylation
Authors Hyojin Park, Kwangho Yoo, Byunghyuck Jung1,*, Min Kim*
Department of Chemistry, Chungbuk Natioanl University, Korea
1School of Basic Science, Daegu Gyeongbuk Institute of Science & Technology, Korea
Abstract Directing groups are essential part for regio-selective transition metal-catalyzed organic reactions. Generally, the first step of transition metal-catalyzed reaction is the formation of coordination bond between directing groups and metal ion (or cluster). However, this directing group approach typically requires the additional steps for the installation and removal of the chelating component, and diminishes the efficiency and compatibility of the reactions in the practical concept. Recently, C-H bond activation reactions using temporary, transient directing groups that can be reversibly linked to the substrate have studied to overcome this issue.[1-3]
In this presentation, our recent results about transient ligand developments for palladium-catalyzed C-H bond activation, especially sp3 C-H arylations will be discussed. The novel amino acid and amino alcohol-based transient directing group reversibly reacts with the aldehydes in the substrate to imine formation. And the palladium catalyst could be positioned, and the inert C–H bond activation and arylation are performed. The preparation of new ligands and their catalytic activities will be presented along with substrate scopes for sp3 C-H bond arylation reactions.


References
[1] Zhang, F.-L.; Hong, K.; Li, T.-J.; Park, H.; Yu, J.-Q. Science, 2016, 351, 252.
[2] Ma, F.; Lei, M.; Hu, L. Org. Lett. 2016, 18, 2708.
[3] Liu, X.-H.; Yu, J.-Q. et. al. J. Am. Chem. Soc, 2017, 139, 888.
E-mail astro99@hanmail.net