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

Ketene formation via catalytic oxygen-atom transfer to vinylidene carbene

Research Project

Project/Area Number 25620077
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionNagoya University

Principal Investigator

YAMAMOTO Yoshihiko  名古屋大学, 創薬科学研究科, 教授 (60283412)

Project Period (FY) 2013-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Keywords遷移金属触媒 / ルテニウム錯体 / アルキン / 多環芳香族化合物 / 複素環化合物 / 環化反応 / 遷移金属錯体 / 触媒
Outline of Final Research Achievements

In the presence of a dicationic ruthenium complex with p-cymene and triphenylphosphine ligands, 2-ethynylbiaryls underwent cycloisomerization to afford phenanthrenes. Heterocyclic anolog of 2-ethynylbiaryls containing furan, thiophene, and pyrrole rings were also transformed into heteropolyaromatic compounds in higher yields. DFT calculations of model systems suggested that the cycloisomerization proceeded with the Friedel-Crfats type cyclization without intermediacy of an expected vinylidene carbene complex.
Furthermore, it was found that a cationic ruthenium complex catalyzed the transfer-oxygenative [2+2+1] cycloaddition of 1,6-diynes with at least one trimethylsilyl terminal, affording bicyclic silylfurans. As the oxygen-atom donor, nitrons proved to be more effective than the previously used DMSO.

Report

(3 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • Research Products

    (4 results)

All 2015 2014

All Journal Article (2 results) (of which Peer Reviewed: 2 results,  Acknowledgement Compliant: 1 results) Presentation (2 results)

  • [Journal Article] A Combined Experimental and Computational Study on the Cycloisomerization of 2-Ethynylbiaryls Catalyzed by Dicationic Ruthenium Complexes2015

    • Author(s)
      Yoshihiko Yamamoto, Kazuma Matsui, Masatoshi Shibuya
    • Journal Title

      Chemistry - A European Journal

      Volume: 21 Issue: 19 Pages: 7245-7255

    • DOI

      10.1002/chem.201500248

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of Heterocycles via Transition-Metal-Catalyzed Hydroarylation of Alkynes2014

    • Author(s)
      Yoshihiko Yamamoto
    • Journal Title

      Chemical Society Reviews

      Volume: 43 Issue: 5 Pages: 1575-1600

    • DOI

      10.1039/c3cs60369e

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] ルテニウム触媒を用いたo-エチニルビアリールの環化異性化反応による多環式芳香族化合物の合成2015

    • Author(s)
      松井一真、澁谷正俊、山本芳彦
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部舟橋キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] ルテニウム触媒を用いたo-エチニルビアリールの環化異性化反応による多環芳香族化合物の合成2014

    • Author(s)
      松井一真、澁谷正俊、山本芳彦
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学病院キャンパス
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Annual Research Report

URL: 

Published: 2014-07-25   Modified: 2019-07-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi