Loading...
2017.05.22 09:36

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

?

Shortcut

PrevPrev Article

NextNext Article

+ - Up Down Comment Print
?

Shortcut

PrevPrev Article

NextNext Article

+ - Up Down Comment Print
Extra Form
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 Spring semester 2017 Seminar Schedule file - -
32 7th Jilin-Korea-Waseda Alliance Annual Symposium file - August 17 ~ 19, 2017
31 [Wed. 5 July. 2017] Seminar was canceled! - -
30 [Fri. 16 Jun. 2017] Prof. Martin Thuo/Department of Materials Science and Engineering, Iowa State University, USA Prof. Martin Thuo Fri. 16 Jun. 2017
29 [Thu. 8 Jun. 2017] Prof. Won-jin Chung/Department of Chemistry, GIST, Gwangju, Republic of Korea Prof. Won-jin Chung Thu. 8 Jun. 2017
28 [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
26 [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
25 [Thu. 11 May. 2017] Prof. Andreas Heinrich/IBS Research, Center for Quantum Nanoscience, Seoul, South Korea Prof. Andreas Heinrich Thu. 11 May. 2017
24 [Thu. 27 Apr. 2017] Seminar was canceled! - -
23 [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
22 [Thu. 6 Apr. 2017] Prof. Rong-Jie Chein/Institute of Chemistry, Academia Sinica, Nankang, Taipei, Taiwan Prof. Rong-Jie Chein Thu. 6 Apr. 2017
21 [Thu. 30 Mar. 2017] Prof. Jeong Ho Cho/SKKU Advanced Institute of Nanotechnology (SAINT), School of Chemical Engineering, Sungkyunkwan University, Suwon, Korea Prof. Jeong Ho Cho Thu. 30 Mar. 2017
20 [Thu. 23 Mar. 2017] Prof. Sangsu Bae/Department of Chemistry, Hanyang University, Seoul, South Korea Prof. Sangsu Bae Thu. 23 Mar. 2017
19 [Fri. 17 Mar. 2017] 9th RINS Symposium file - Fri. 17 Mar. 2017
18 [Thu. 9 Mar. 2017] Prof. Woon Ju Song/Department of Chemistry, Seoul National University, Seoul, Korea Prof. Woon Ju Song Thu. 9 Mar. 2017
17 [Mon. 9 Jan. 2017] Prof. Sungwook Woo/Wyss Institute for Biologically Inspired Engineering, Harvard University, USA Prof. Sungwook Woo Mon. 9 Jan. 2017
16 [Wed. 28 Dec. 2016] Prof. James Y. Hamilton/Development of a Broad Range of Asymmetric C–C Bond Forming Reactions with a Versatile Iridium Catalyst file Prof. James Y. Hamilton Wednesday 28 December 2016
15 [Thu. 1 Dec. 2016] Prof. Sang-Yong Ju/Highly Pure Carbon Nanotubes sorted by a Flavin for Thin Film Transistor Applications Prof. Sang-Yong Ju Thursday 1 December 2016
14 [Thu. 17 Nov. 2016] Prof. Seunghoon Shin/Synthetic Methods Development based on Rational Analysis of Intermediates file Prof. Seunghoon Shin Thursday 17 November 2016
Board Pagination ‹ Prev 1 2 Next ›
/ 2

Designed by sketchbooks.co.kr / sketchbook5 board skin

나눔글꼴 설치 안내


이 PC에는 나눔글꼴이 설치되어 있지 않습니다.

이 사이트를 나눔글꼴로 보기 위해서는
나눔글꼴을 설치해야 합니다.

설치 Cancel

Sketchbook5, 스케치북5

Sketchbook5, 스케치북5

Sketchbook5, 스케치북5

Sketchbook5, 스케치북5

Department of Chemistry, Korea University, Tel) +82-2-3290-3120
145 Anam-ro Seongbuk-gu Seoul, 02841, Republic of Korea
Copyright(c) 2014 KOREA UNIVERSITY DEPARTMENT of CHEMISTRY. All right reserved.