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


  1. Fall semester 2016 Seminar Schedule

    -
    -
    Read More
  2. Spring semester 2017 Seminar Schedule

    -
    -
    Read More
  3. [Fri. 17 Mar. 2017] 9th RINS Symposium

    -
    Fri. 17 Mar. 2017
    Read More
  4. [Thu. 27 Apr. 2017] Seminar was canceled!

    -
    -
    Read More
  5. [Wed. 5 July. 2017] Seminar is canceled!

    -
    -
    Read More
  6. 7th Jilin-Korea-Waseda Alliance Annual Symposium

    -
    August 17 ~ 19, 2017
    Read More
  7. Fall semester 2017 Seminar Schedule

    -
    -
    Read More
  8. Fall semester 2018 Seminar Schedule

    -
    -
    Read More
  9. Spring semester 2019 Seminar Schedule

    -
    -
    Read More
  10. Announcements Graduate Seminar Spring Semester 2021

    .
    .
    Read More
  11. Announcement for Graduate Seminar Class, Fall Semester 2020

    Announcement for Graduate Seminar Class, Fall Semester 2020
    Announcement for Graduate Seminar Class, Fall Semester 2020
    Read More
  12. [October 31. 2019] Engineering energy band structures in organic and hybrid semiconductor devices using non-conjugated polyelectrolyte films

    Asst. Prof. Bright Walker(Kyung Hee University)
    Thu. 31 October. 2019
    Read More
  13. June 10th (Fri) Graduate Seminar / Bing Zhang, Ph.D.

    Bing Zhang, Ph.D. (Baylor College of Medicine)
    Fri, Jun 10, 2022
    Read More
  14. 2022 International Symposium on Bioactive and Bioengineering Materials

    BK21 Chemistry Education Research Center
    November 22, 2022 (Tuesday)
    Read More
  15. 2022 International Symposium on Chemical Applications of Machine Learning

    BK21 Chemistry Education Research Center
    November 11, 2022 (Fri)
    Read More
  16. 2023 Germany-Korea On-Site Plenary Discussion on Computational Electrochemistry

    BK21 Chemistry Education Research Center
    April 17, 2023 (Mon)
    Read More
  17. [October 10, 2017] Novel Terahertz Spectroscopies

    Director Mischa Bonn
    Tue, October 10, 2017
    Read More
  18. [August 14. 2019] Principle of Semiconductor Quantum Cascade Laser and It’s Application to Chemical Gas Detection

    Dr. Byeong-il Seo(Agency for Defense Development)
    Wed. 14 August. 2019
    Read More
  19. [October 25, 2017] Ultrafast electron microscopy: applications in chemical and materials sciences

    Dr. Byung-Kuk Yoo
    October 25, 2017
    Read More
  20. May 11, 2023 (Thu) Dr. Changyeol Lee

    Dr. Changyeol Lee (Advanced Photonics Research Institute GIST)
    Thursday, May 11, 2023
    Read More
Board Pagination ‹ Prev 1 2 3 4 5 6 7 8 Next ›
/ 8

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.