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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 2018 Seminar Schedule file - -
50 Fall semester 2016 Seminar Schedule file - -
49 [Fri. 17 Mar. 2017] 9th RINS Symposium file - Fri. 17 Mar. 2017
48 Spring semester 2017 Seminar Schedule file - -
47 Fall semester 2017 Seminar Schedule file - -
46 [Thu. 27 Apr. 2017] Seminar was canceled! - -
45 [Wed. 5 July. 2017] Seminar is canceled! - -
44 7th Jilin-Korea-Waseda Alliance Annual Symposium file - August 17 ~ 19, 2017
43 [October 10, 2017] Novel Terahertz Spectroscopies file Director Mischa Bonn Tue, October 10, 2017
42 [October 25, 2017] Ultrafast electron microscopy: applications in chemical and materials sciences Dr. Byung-Kuk Yoo October 25, 2017
41 [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
40 [Thu. 26 Oct. 2017] Dr. Jung-Nyoung Heo/Center for Medicinal Chemistry Research, Korea Research Institute of Chemical Technology, Daejeon, Korea Dr. Jung-Nyoung Heo Thu. 26 Oct. 2017
39 [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
38 [Mon. 13 Oct. 2016] Prof. Amir H. Hoveyda/Multicomponent Catalytic Synthesis of Organoboron Compounds for Scalable Natural Product Synthesis Prof. Amir H. Hoveyda Monday 13 October 2016
37 [Thu. 11 May. 2017] Prof. Andreas Heinrich/IBS Research, Center for Quantum Nanoscience, Seoul, South Korea Prof. Andreas Heinrich Thu. 11 May. 2017
36 [Thu. 22 Sep. 2016] Prof. Anna Lee/Organocatalyzed Asymmetric Reactions Prof. Anna Lee Thursday 22 September 2016
35 [Thu. 20 Oct. 2016] Prof. Chan Hyuk Kim/Novel Small Molecule-based Approaches for Cancer Immunotherapy Prof. Chan Hyuk Kim Thursday 20 October 2016
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 [Thu. 6 Dec. 2018] Prof. Dong-Ho Kim/Department of Chemistry, Yonsei University, Seoul, Korea Prof. Dong-Ho Kim (Yonsei University) Thu. 6 Dec. 2018
32 [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
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