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2017.05.22 09:36

[Thu. 25 May. 2017] Prof. Wonsuk Kim/Department of Chemistry and Nano Science, Ewha Womans University, Seoul

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Speaker Prof. Wonsuk Kim
Date Thu. 25 May. 2017
Time 5:00pm
Venue #633, Asan Hall, College of Science

“Chemoselective C-C/C-N Bond Formation Reactions”

 

 

N-Arylpyridine-2-ones are a ubiquitous moiety present in many bioactive compounds and pharmaceutical drugs. Due to their intriguing biological activities such as antifibrotic, anti-inflammatory, anticonvulsant, and sedative activities, several copper-catalyzed coupling reactions for C-N bond formation between 2-pyridones and electrophiles such as aryl boronic acids, aryl stannanes, aryl bismuth, and aryl halides have been previously reported. Herein, to explain the viability of diaryliodonium salts as an electrophilic coupling partner, we report copper-catalyzed C-N bond formation using 2-pyridone derivatives at room temperature.

Heterocycles including pyridine are one of the most widely studied classes. Pyridine and its derivatives are easily found in natural products and of great importance in synthetic chemistry, pharmaceutical and agrochemical research. Therefore, numerous synthetic methods have been reported to form functionalized pyridines. Palladium catalyzed cross coupling reaction is one of the most convenient and versatile method for the preparation of trisubstituted pyridines from polyhalogenated pyridines. Therefore, chemoselective Suzuki-Miyaura reactions on 3,5- and 4,6-dibromo-2-tosyloxypyridine have been studied. The optimized conditions allow for a facile access to 3,5- and 4,6-diaryl-2-tosyloxypyridines in yields of 8 to 99%. Further functionalization of the tosylate group in the diarylpyridine derivatives obtained was accomplished for the synthesis of novel and biologically relevant trisubstituted pyridines. The formal synthesis of ficuseptine has also been achieved in 5 steps from 3,5-dibromo-2-hydroxypyridine with 50% overall yield.

Finally, we employed the benzyne intermediate formed by 1,3-silyl group migration on the aryl moiety to demonstrate metal-free C-N bond formation. This base-promoted benzyne formation method would be used for the synthesis of 3-aminophenol or carbazole derivatives, which are the scaffold of some synthetic compounds with various pharmacological activities.

 

Prof. Wonsuk Kim

Department of Chemistry and Nano Science, Ewha Womans University, Seoul


List of Articles
No. Subject Speaker Date
Notice Fall semester 2017 Seminar Schedule file - -
41 [Thu. 26 Oct. 2017] Dr. Jung-Nyoung Heo/Center for Medicinal Chemistry Research, Korea Research Institute of Chemical Technology, Daejeon, Korea new Dr. Jung-Nyoung Heo Thu. 26 Oct. 2017
40 [October 25, 2017] Ultrafast electron microscopy: applications in chemical and materials sciences new Dr. Byung-Kuk Yoo October 25, 2017
39 [Mon. 16 Oct. 2017] Prof. Kirk S. Schanze/Department of Chemistry, University of Texas at San Antonio, Texas, USA Prof. Kirk S. Schanze Mon. 16 Oct. 2017
38 [Fri. 13 Oct. 2017] Dr. J. Nathan Hohman/The Molecular Foundry, Lawrence Berkeley National Laboratory, California, USA Dr. J. Nathan Hohman Fri. 13 Oct. 2017
37 [Thu. 12 Oct. 2017] Student Host Colloquium : Versatile Dendrimer-Encapsulated Nanoparticles for Analytical Applications Prof. Joohoon Kim Thu. 12 Oct. 2017
36 [October 10, 2017] Novel Terahertz Spectroscopies file Director Mischa Bonn Tue, October 10, 2017
35 [Thu. 28 Sep. 2017] Prof. Eunsung Lee/Department of Chemistry, POSTECH and Center for Self–assembly and Complexity, Institute for Basic Science (IBS), Pohang, Republic of Korea Prof. Eunsung Lee Thu. 28 Sep. 2017
34 [Thu. 14 Sep. 2017] Prof. Dokyoung Kim/Department of Anatomy and Neurobiology, Kyung Hee University, Seoul Prof. Dokyoung Kim Thu. 14 Sep. 2017
33 7th Jilin-Korea-Waseda Alliance Annual Symposium file - August 17 ~ 19, 2017
32 [Wed. 5 July. 2017] Seminar is canceled! - -
31 [Fri. 16 Jun. 2017] Prof. Martin Thuo/Department of Materials Science and Engineering, Iowa State University, USA Prof. Martin Thuo Fri. 16 Jun. 2017
30 [Thu. 8 Jun. 2017] Prof. Won-jin Chung/Department of Chemistry, GIST, Gwangju, Republic of Korea Prof. Won-jin Chung Thu. 8 Jun. 2017
29 [Thu. 1 Jun. 2017] Prof. Jong-Man Kim/Department of Chemical Engineering, Hanyang University, Seoul, Korea Prof. Jong-Man Kim Thu. 1 Jun. 2017
» [Thu. 25 May. 2017] Prof. Wonsuk Kim/Department of Chemistry and Nano Science, Ewha Womans University, Seoul Prof. Wonsuk Kim Thu. 25 May. 2017
27 [Thu. 18 May. 2017] Student Host Colloquium : 1,1-Bisborylalkane: New Class of Organoboron Compound for the Chemo, Regio and Stereoselective Organic Transformations Prof. Seung Hwan Cho Thu. 18 May. 2017
26 [Thu. 11 May. 2017] Prof. Andreas Heinrich/IBS Research, Center for Quantum Nanoscience, Seoul, South Korea Prof. Andreas Heinrich Thu. 11 May. 2017
25 [Thu. 27 Apr. 2017] Seminar was canceled! - -
24 [Thu. 13 Apr. 2017] Dr. Wan Ki Bae/Photoelectronic Hybrid Research Center, Korea Institute of Science and Technology, Seoul, Korea Dr. Wan Ki Bae Thu. 13 Apr. 2017
23 [Thu. 6 Apr. 2017] Prof. Rong-Jie Chein/Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan Prof. Rong-Jie Chein Thu. 6 Apr. 2017
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