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. [Fri. 30 Oct. 2017] Prof. Igor Rodin/Department of Chemistry, Moscow State University, Moscow, Russia

    Prof. Igor Rodin
    Fri. 30 Oct. 201
    Read More
  2. [Thu. 8 Sep. 2016] Prof. Jaeyoung Sung/Stochastic chemical dynamics in living cells and its consequence for the control capacity of living cells over biological functions

    Prof. Jaeyoung Sung
    Thursday 8 September 2016
    Read More
  3. [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

    Prof. James Y. Hamilton
    Wednesday 28 December 2016
    Read More
  4. [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
    Read More
  5. [Fri. 17 Jun. 2016] Prof. Jianwei Sun/Remote Control in Brønsted Acid Catalysis: New Strategies for the Synthesis of Chiral Building Blocks and Medium Rings

    Prof. Jianwei Sun
    Friday 17 June 2016
    Read More
  6. [March 21, 2019] Nanomaterials Design for Energy Conversion and Storage

    Prof. Jong-Hyuk Park (Yonsei University)
    Thu. 21 Mar. 2019
    Read More
  7. [Thu. 1 Jun. 2017] Prof. Jong-Man Kim/Department of Chemical Engineering, Hanyang University, Seoul, Korea

    Prof. Jong-Man Kim
    Thu. 1 Jun. 2017
    Read More
  8. [Thu. 12 Oct. 2017] Student Host Colloquium : Versatile Dendrimer-Encapsulated Nanoparticles for Analytical Applications

    Prof. Joohoon Kim
    Thu. 12 Oct. 2017
    Read More
  9. November 4th (Thu) Graduate Seminar / Prof. Junpei Kuwabara

    Prof. Junpei Kuwabara (Tsukuba Research Center for Interdisciplinary Materials Science (TREMS), Graduate School of Pure and Applied Sciences, University of Tsukuba)
    Thursday, November 4, 2021
    Read More
  10. [April 4. 2019] Rational Design of Solid-State Materials with Asymmetric Coordination Environment

    Prof. Kang Min Ok (Sogang University)
    Thu. 4 Apr. 2019
    Read More
  11. November 25th (Thu) Graduate Seminar / Prof. Kanyi Pu

    Prof. Kanyi Pu (School of Chemical and Biomedical Engineering; School of Physics and Mathematical Science; Lee Kong Chian School of Medicine, Nanyang Technological University, Singapore)
    Thursday, November 25, 2021
    Read More
  12. [March 27, 2019] Hyperpolarization Researches with NV center, 129Xe and Parahydrogen

    Prof. Keunhong Jeong
    March 27, 2019
    Read More
  13. [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
    Read More
  14. [Fri. 16 Jun. 2017] Prof. Martin Thuo/Department of Materials Science and Engineering, Iowa State University, USA

    Prof. Martin Thuo
    Fri. 16 Jun. 2017
    Read More
  15. [March 5. 2019] Prof. Michael J. Sailor/Treatment of S. aureus Bacterial Infections with Porous Silicon Nanoparticles

    Prof. Michael J. Sailor (UC San Diego)
    Tuesday. 5 March. 2019
    Read More
  16. [November 14, 2017] Zero-Point Energy, Fluctuations, and Dissipation : A (Mostly) Quantum-Optical Perspective

    Prof. Milonni, Peter
    November 14, 2017
    Read More
  17. [Thu. 3 Nov. 2016] Prof. Min-Sik Kim/Mass spectrometry and its applications to Biological Discovery

    Prof. Min-Sik Kim
    Thursday 3 November 2016
    Read More
  18. [January 24, 2018] Electro-Optic Organic THz Wave Sources

    Prof. O-Pil Kwon(Ajou University)
    January 24, 2018 (Wednesday)
    Read More
  19. [May 9. 2019] Chemistry in Molecular Vessels

    Prof. Partha Sarathi Mukherjee
    Thu. 9 May. 2019
    Read More
  20. [October 31, 2017] New ways of vision: Protein structures in translational medicine and business development, my experience

    Prof. Robert Huber(1988 Nobel Prize in Chemistry)
    October 31, 2017
    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.