121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-481
Subject Direct Synthesis of Anthracenes via Tandem Reaction: Pd-Catalyzed sp3 C-H Arylation using Transient Ligands
Authors Kwangho Yoo, Byunghyuck Jung1,*, Min Kim*
Department of Chemistry, Chungbuk National University, Korea
1School of Basic Science, Daegu Gyeongbuk Institute of Science & Technology, Korea
Abstract Anthracenes are polycyclic aromatic hydrocarbon, and consisting of three fused benzene rings. Anthracene derivatives could be used as chromophores in various applications such as bio-probes, lighting-emitting devices, and polycyclic aromatic drugs. There are several reported procedures for the direct preparation of anthracene derivatives. However, it usually requires complex substrates that demand multistep syntheses and show poor functional group tolerances. To solve this problem, we recently have studied the direct synthesis of anthracene through tandem reaction of Pd-catalyzed sp3 C-H arylation and electrophilic aromatic cyclization.
In this presentation, first of all, novel amino acid-based transient ligand development for the first step, palladium-catalyzed C-H bond arylation reaction will be discussed. The new transient directing group reversibly reacts with the aldehydes to imine formation. And the palladium could be positioned and activate the inert C–H bonds by this temporary directing group.[1-3] The preparation of new ligands and their catalytic activities will be presented along with substrate scopes for sp3 C-H bond arylation reactions. And the direct synthesis of anthracenes will also be discussed. From the reaction between o-tolualdehydes and aryl iodides, the anthracene derivatives were obtained. The selectivity from silver oxidant, and the substrate scope for anthracenes will be presented.

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. J. Am. Chem. Soc. 2017, 139, 888.
E-mail kwangho6313@gmail.com