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

The development of a first low transition metal catalyzed method for multi-substituted olefins from organo halides

Research Project

Project/Area Number 15K05502
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionHiroshima University

Principal Investigator

Kimihiro Komeyama  広島大学, 工学研究科, 助教 (80432681)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2016: ¥1,300,000 (Direct Cost: ¥1,000,000、Indirect Cost: ¥300,000)
Fiscal Year 2015: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
Keywords第1遷移金属触媒 / コバルト / ニッケル / 有機ハロゲン / 多置換オレフィン / ユビキタス金属触媒 / アルキン / アレン / カルボメタル化反応 / ビスアリル化反応 / 3成分カップリング反応 / 第一遷移金属触媒 / ビスベンジル化反応 / スタニル化反応 / ホウ素化反応
Outline of Final Research Achievements

Multi-substituted olefins are important functional skeletons contained in pharmaceuticals and organic materials. For this reason, various methods have been developed and studied so far. However, in the conventional method, the carbometalation using a highly reactive organometallic reagent is generally a synthetic route, but the problem is a low compatibility for functional group and strict reaction conditions due to their high reactivity. In this study, we have explored the efficient method for multi-substituted olefin synthesis by multi-functionalization of alkynes starting from organic halide utilizing the potential reducing ability and alkyne-affinity of ubiquitous metal catalyst, cobalt and nickel catalysts.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (22 results)

All 2018 2017 2016 2015 Other

All Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results,  Acknowledgement Compliant: 5 results,  Open Access: 2 results) Presentation (11 results) (of which Invited: 2 results) Remarks (3 results)

  • [Journal Article] Nickel-catalyzed reductive bis-allylation of alkynes2018

    • Author(s)
      Kimihiro Komeyama, Yuta Yamahata, Itaru Osaka
    • Journal Title

      Org. Lett.

      Volume: 20 Issue: 5 Pages: 1457-1460

    • DOI

      10.1021/acs.orglett.8b00235

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Naphthobispyrazine as an Electron-deficient Building Unit for π-Conjugated Polymers: Efficient Synthesis and Polymer Properties2017

    • Author(s)
      Tsubasa Mikie, Kazuaki Kawashima, Kimihiro Komeyama, Hiroto Yoshida, and Itaru Osaka
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 8 Pages: 1193-1196

    • DOI

      10.1246/cl.170445

    • NAID

      130005906952

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] NHC-catalyzed cleavage of vicuna diketones and triketones followed by insertion of nones and ynones2017

    • Author(s)
      Ken Takaki, Hino Maroto, Akira Ohno, Kimihiro Komeyama, Hiroto Yoshida, Hiroshi Fukuoka
    • Journal Title

      Beilstein J. Org, Chem.

      Volume: 13 Pages: 1816-1822

    • DOI

      10.3762/bjoc.13.176

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Highly nucleophilic vitamin B12-assisted nickel-catalysed reductive coupling of aryl halides and non-activated alkyl tosylates2017

    • Author(s)
      Kimihiro Komeyama, Ryo Ohata, Shinnosuke Kiguchi, Itaru Osaka
    • Journal Title

      Chemical Communications

      Volume: 53 Issue: 48 Pages: 6401-6404

    • DOI

      10.1039/c7cc01932g

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Practical stannylation of allyl acetates catalyzed by Nickel with Bu3SnOMe2016

    • Author(s)
      Kimihiro Komeyama, Yuuhei Itai, Ken Takaki
    • Journal Title

      Chemistry - A European Journal

      Volume: - Issue: 27 Pages: 9130-9134

    • DOI

      10.1002/chem.201601515

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] The drastic effect of cobalt and chromium catalysts in the borylation of arylzinc reagents2016

    • Author(s)
      Kimihiro Komeyama, Shinnosuke Kiguchi, Ken Takaki
    • Journal Title

      Chemical Communications

      Volume: 52 Issue: 43 Pages: 7009-7012

    • DOI

      10.1039/c6cc03086f

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Cobalt-catalyzed intermolecular stereoselective bisbenzylation of alkynes2015

    • Author(s)
      Kimihiro Komeyama, Ryota Asakura, Hiroshi Fukuoka, Ken Takaki
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 13 Pages: 1735-1737

    • DOI

      10.1016/j.tetlet.2015.02.101

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Sn atom-economical approach toward arylstannanes: Ni-catalyzed stannylation of aryl halides using Bu3SnOMe2015

    • Author(s)
      Kimihiro Komeyama, Ryota Asakura, Ken Takaki
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 13 Issue: 32 Pages: 8713-8716

    • DOI

      10.1039/c5ob01096a

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Presentation] 有機反応開発における電子実験ノートの使用例2018

    • Author(s)
      米山公啓
    • Organizer
      第98回日本化学会春季年会 特別企画:研究記作成の重要性とアカデミアでの電子実験ノート活用の提案
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] ニッケル/コバルト触媒系を利用する脂肪族トシラートをラジカル源として用いたsp3炭素-sp3炭素クロスカップリング反応2018

    • Author(s)
      道行拓哉、尾坂格、米山 公啓
    • Organizer
      第98回日本化学会春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ニッケル/コバルト触媒系による有機ハロゲン化物のメチル化反応2018

    • Author(s)
      山畑勇太、尾坂格、米山 公啓
    • Organizer
      第98回日本化学会春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] コバルト/クロム触媒系による芳香族ハロゲン化物の化学変換2017

    • Author(s)
      米山公啓、木口真之介、岩下健杜、尾坂格
    • Organizer
      第111回有機合成シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ni/VB12触媒系による脂肪族トシラートを用いた還元的カップリング反応2017

    • Author(s)
      米山公啓
    • Organizer
      第4回辰巳午化学シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Ni/Co-Catalyzed Cross-Coupling Reaction Using Alkyl Tosylates as Carbon Sources2017

    • Author(s)
      Kimihiro Komeyama, Ryo Ohata, Shinnosuke Kiguchi, Takuya Michiyuki, Itaru Osaka
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ニッケル/ビタミンB12触媒系によるアルキルトシラートを用いたクロスカップリング反応2017

    • Author(s)
      米山公啓、大畠遼、木口真之介、道行拓哉、尾坂格
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] Co/Cr 触媒系による芳香族ハロゲン化物の求電子的ホウ素化反応2016

    • Author(s)
      米山公啓、木口真之介、高木謙
    • Organizer
      第96回日本化学会春季年会
    • Place of Presentation
      同志社大学・京田辺キャンパス(京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Nickel-catalyzed stannylation of aryl halides and allyl acetates2016

    • Author(s)
      KOMEYAMA, Kimihiro; ASAKURA, Ryota, ITAI, Yuuhei, TAKAKI Ken
    • Organizer
      第96回日本化学会春季年会
    • Place of Presentation
      同志社大学・京田辺キャンパス(京都府・京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] Nickel-catalyzed stannylation of organo halides2015

    • Author(s)
      米山公啓、朝倉遼太、板井祐平、高木謙
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学・千里山キャンパス(大阪府・吹田市)
    • Year and Date
      2015-09-07
    • Related Report
      2015 Research-status Report
  • [Presentation] コバルトおよびニッケル触媒を用いた炭素-ハロゲン結合の化学変換2015

    • Author(s)
      米山公啓
    • Organizer
      第50回有機反応若手の会夏の学校
    • Place of Presentation
      中央森林公園・広島(広島県・三原市)
    • Year and Date
      2015-07-29
    • Related Report
      2015 Research-status Report
    • Invited
  • [Remarks] 広島大学大学院工学研究科応用化学専攻 反応設計化学研究室

    • URL

      http://home.hiroshima-u.ac.jp/~rdc/

    • Related Report
      2017 Annual Research Report
  • [Remarks] Publications - Kimihiro Komeyama

    • URL

      https://www.evernote.com/l/ADWPmBcpogZApJg2kw4_eAXNmkRes2GOeg4

    • Related Report
      2017 Annual Research Report
  • [Remarks] 広島大学大学院工学研究院応用化学専攻 反応設計化学研究室

    • URL

      http://home.hiroshima-u.ac.jp/~rdc/

    • Related Report
      2015 Research-status Report

URL: 

Published: 2015-04-16   Modified: 2019-03-29  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi