• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

2004 Fiscal Year Final Research Report Summary

Combination of Reactions and Separations for New Organic Synthesis

Research Project

Project/Area Number 14205125
Research Category

Grant-in-Aid for Scientific Research (A)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKyoto University

Principal Investigator

YOSHIDA Jun-ichi  Kyoto University, Graduate School of Engineering, Professor, 工学研究科, 教授 (30127170)

Co-Investigator(Kenkyū-buntansha) ITAMI Kenichiro  Kyoto University, Graduate School of Engineering, Assistant Professor, 工学研究科, 助手 (80311728)
Project Period (FY) 2002 – 2004
Keywordsstrategic separation / acid-base extraction / phase tag / pyridylsilyl group / diversity oriented synthesis / library of p-electron systems
Research Abstract

The purpose of organic synthesis is to produce useful organic compounds with high efficiency. Organic chemists have tended to focus on the efficiency of reactions and competence of synthetic strategies. It is important to recognize, however, that total efficiency of synthesis is also limited by the ability to separate and isolate products in a pure form. Although substantial efforts have been made to develop new efficient reactions, it is highly necessary to develop strategic separation protocols that are generally applicable for various structural types of compounds. The purpose of this research is developing a new combination of strategic separation protocol and reactions to enhance the ability of organic synthesis.
We focused on acid-base extraction and found that 2-pyridyldimethylsilyl group serves as an effective phase tag for this purpose. The introduction of the tag to organic molecules can be easily accomplished by hydrosilylation and the reaction with 2-pyridylsilylmethyllithium. Carbometallation (Mizoroki-Heck reaction) to alkenylpyrilylsilane and alkynylpyridylsilane can also be utilized for the synthesis of tagged compounds. The removal of the tag can be accomplished by Tamao oxidation and Hiyama cross-coupling reaction.
With the tag in hand, we have developed diversity oriented synthesis of biologically active compounds such as tamoxifen type tetrasubstituted olefins. We also developed new methods for the construction of extended π-electron systems, which exhibit interesting photophysical properties such as photo luminescence. By using difunctional and trifunctional aryl halides in Mizoroki-Heck reactions and cross-coupling reactions, unique polymers and dendrimers of extended π-electron systems were synthesized.

  • Research Products

    (6 results)

All 2004

All Journal Article (5 results) Book (1 results)

  • [Journal Article] Sequential Assembly Strategy for Tetrasubstituted Olefin Synthesis Using Vinyl 2-Pyrimidyl Sulfide as a Platform2004

    • Author(s)
      K.Itami, M.Mineno, N.Muraoka, J.Yoshida
    • Journal Title

      J.Am.Chem.Soc. 126

      Pages: 11778-11779

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Catalytic Intermolecular Pauson-Khand-type Reaction : Strong Directing Effect of Pyridylsilyl and Pyrimidylsilyl Groups and Isolation of Ru Complexes Relevant to Catalytic Reaction2004

    • Author(s)
      K.Itami, K.Mitsudo, K.Fujita, Y.Ohashi, J.Yoshida
    • Journal Title

      J.Am.Chem.Soc. 126

      Pages: 11058-11066

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Pyrimidine-Core Extended π-Systems : General Synthesis and Interesting Fluorescent Properties2004

    • Author(s)
      K.Itami, D.Yamazaki, J.Yoshida
    • Journal Title

      J.Am.Chem.Soc. 126

      Pages: 15396-15397

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Catalytic Carbometalation/Cross-Coupling Sequence Across Alkynyl(2-pyridyl)silanes Leading to a Diversity-Oriented Synthesis of Tamoxifen-type Tetrasubstituted Olefin2004

    • Author(s)
      T.Kamei, K.Itami, J.Yoshida
    • Journal Title

      Adv.Synth.Catal. 346

      Pages: 1824-1835

    • Description
      「研究成果報告書概要(和文)」より
  • [Journal Article] Catalytic Carbometalation/Cross-Coupling Sequence Across Alkynyl(2-pyridyl)silanes Leading to a Diversity-Oriented Synthesis of Tamoxifen-type Tetrasubstituted Olefins2004

    • Author(s)
      T.Kamei, K.Itami, J.Yoshida
    • Journal Title

      Adv.Synth.Catal. 346

      Pages: 1824-1835

    • Description
      「研究成果報告書概要(欧文)」より
  • [Book] ロボット・マイクロ合成最前線-有機合成の新戦略2004

    • Author(s)
      吉田潤一
    • Total Pages
      188
    • Publisher
      化学同人
    • Description
      「研究成果報告書概要(和文)」より

URL: 

Published: 2006-07-11  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi