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Development of novel carbon-carbon bond formation with abnormal regioselectivity by commercially available main group elements

Research Project

Project/Area Number 25410110
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionNagaoka University of Technology

Principal Investigator

Maekawa Hirofumi  長岡技術科学大学, 工学(系)研究科(研究院), 教授 (70283041)

Co-Investigator(Kenkyū-buntansha) YAMAMOTO Yoshimasa  東京工業高等専門学校, 物質工学科, 准教授 (90444190)
Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2013: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywordsマグネシウム / 電子移動 / 還元 / 環境調和 / 有機合成 / カップリング
Outline of Final Research Achievements

In this study, magnesium-promoted reductive introduction of a functional group to aromatic compounds was investigated because magnesium is commercially available and relatively cheap. Moreover, an abnormal and regioselective carbon-carbon bond formation was a special theme in this coupling reaction. As a result, next reactions with a carbon-carbon bond or carbon-silicon bond formation were found in this research.; fixation of carbon dioxide to carbonyl group of benzoic acid esters, synthesis of acetylenic compounds with the transposition of the triple bond from aromatic conjugated ynones under acylation conditions, silylation of vinylpyridines at the terminal carbon atom of the vinyl group and double silylation of cinnamic acid esters with a leaving group at beta-position of the carbonyl group.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • 2013 Research-status Report
  • Research Products

    (30 results)

All 2016 2015 2014 2013 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results,  Acknowledgement Compliant: 4 results) Presentation (18 results) (of which Invited: 2 results) Book (3 results) Remarks (2 results)

  • [Journal Article] Facile and highly selective silylation of vinylpyridines at the beta-olefinic carbon by magnesium-promoted reduction2016

    • Author(s)
      T. Zhang, Z. Zhang, Y. Nishiyama, H. Maekawa
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 18 Pages: 2293-2299

    • DOI

      10.1016/j.tet.2016.03.042

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Selective Introduction of a Trifluoroacetyl Group onto 4-Vinylpyridines through Magnesium-Promoted Reduction2015

    • Author(s)
      H. Maekawa, Y. Nishiyama
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 38 Pages: 6694-6700

    • DOI

      10.1016/j.tet.2015.07.046

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Magnesium-promoted reductive acylation of aromatic conjugated ynones accompanying with transposition of the triple bond2015

    • Author(s)
      Tianyuan Zhang, Atsushi Takano, Yutaro Nishiyama, Hirofumi Maekawa
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 18 Pages: 2629-2635

    • DOI

      10.1016/j.tet.2015.03.044

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Facile synthesis of multifunctionalized allenes by magnesium-promoted reductive silylation of aromatic conjugated ynones2014

    • Author(s)
      Hirofumi Maekawa, Atsushi Takano, Masamitsu Watanabe
    • Journal Title

      Tetrahedron Letters

      Volume: 55 Issue: 45 Pages: 6208-6211

    • DOI

      10.1016/j.tetlet.2014.09.066

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Facile synthesis of aromatic unsymmetrical fluorine-containing acyloins through the reductive trifluoroacetylation of benzaldehyde and transposition of the carbonyl group2014

    • Author(s)
      H. Maekawa, M. Kudo, Y. Nishiyama, K. Shimizu, M. Abe
    • Journal Title

      Tetrahedron

      Volume: 70 Issue: 12 Pages: 2081-2087

    • DOI

      10.1016/j.tet.2014.02.016

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Anodic Cyanation of Arylsilanes without Elimination of Silyl Groups2013

    • Author(s)
      H. Maekawa, T. Nakamura, A. Yamaguchi
    • Journal Title

      Electrochemistry

      Volume: 81 Issue: 5 Pages: 394-398

    • DOI

      10.5796/electrochemistry.81.394

    • NAID

      10031152011

    • ISSN
      1344-3542, 2186-2451
    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Magnesium-promoted Reductive Silylation and Acylation of Tropone and Tropone Acetal2013

    • Author(s)
      H. Maekawa, K. Nagakubo, M. Nishi, M. Nishimura, D. Nagahara
    • Journal Title

      Bulletin of the Chemical Society of Japan

      Volume: 86 Issue: 10 Pages: 1183-1189

    • DOI

      10.1246/bcsj.20130156

    • NAID

      10031201274

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 脱離基を有する桂皮酸エチルのマグネシウム還元シリル化反応2016

    • Author(s)
      野田克哲,前川博史
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヒドロキシ基を脱離基とするサリチル酸エステルの電子移動型還元反応2016

    • Author(s)
      金澤 信之祐,前川 博史
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Reductive Trifluoroacetylation of Aromatic Ynones by Electron Transfer from Magnesium2016

    • Author(s)
      T. ZHANG, H. MAEKAWA
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] エステルのβ位に脱離基を有する桂皮酸エチルのマグネシウム還元シリル化反応2015

    • Author(s)
      野田克哲,前川博史
    • Organizer
      第70回記念有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      長岡工業高等専門学校
    • Year and Date
      2015-11-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] エステルのβ位に脱離基を有する桂皮酸エチルのマグネシウム還元シリル化反応2015

    • Author(s)
      野田克哲,前川博史
    • Organizer
      第32回有機合成化学セミナー
    • Place of Presentation
      ニューウェルシティ湯河原
    • Year and Date
      2015-09-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] 出藍に挑むマグネシウム金属還元法2015

    • Author(s)
      前川博史
    • Organizer
      第11回有機電子移動化学若手の会
    • Place of Presentation
      矢太樓
    • Year and Date
      2015-06-27
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 芳香族α,β-不飽和エステル類のマグネシウム還元シリル化反応における脱離基の効果2015

    • Author(s)
      野田克哲,前川博史
    • Organizer
      第39回有機電子移動化学討論会
    • Place of Presentation
      長崎大学
    • Year and Date
      2015-06-25
    • Related Report
      2015 Annual Research Report
  • [Presentation] Mg-Promoted Reductive Silylation of 4-Vinylpyridines2015

    • Author(s)
      T. ZHANG, H. MAEKAWA
    • Organizer
      第69回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      横浜国立大学
    • Year and Date
      2015-05-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] Mg-Promoted Reductive Acylation of Aromatic Conjugated Ynones Accompanying with Transposition of the Triple Bond2015

    • Author(s)
      張田原,西山侑太郎,前川博史
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 芳香族共役エステル類のマグネシウム金属還元によるトリフルオロアセチル化反応2015

    • Author(s)
      安部光弘,清水一行,前川博史
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学(千葉県船橋市)
    • Year and Date
      2015-03-27
    • Related Report
      2014 Research-status Report
  • [Presentation] 芳香族共役エステル類の電子移動型還元によるトリフルオロアセチル化反応2014

    • Author(s)
      安部光弘,清水一行,前川博史
    • Organizer
      第68回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟大学(新潟県新潟市)
    • Year and Date
      2014-11-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 芳香族α,β-不飽和エステル類の電子移動型還元によるトリフルオロアセチル化反応2014

    • Author(s)
      安部光弘,清水一行,吉澤美沙紀,前川博史
    • Organizer
      2014年電気化学秋季大会
    • Place of Presentation
      北海道大学(北海道札幌市)
    • Year and Date
      2014-09-28
    • Related Report
      2014 Research-status Report
  • [Presentation] 4-ビニルピリジン類の金属マグネシウム還元によるトリフルオロアセチル基導入反応2014

    • Author(s)
      前川博史,西山侑太郎
    • Organizer
      第38回有機電子移動化学討論会
    • Place of Presentation
      長良川国際会議場(岐阜県岐阜市)
    • Year and Date
      2014-06-26
    • Related Report
      2014 Research-status Report
  • [Presentation] Mg-Promoted Reductive Acylation of Phenylacetylene Derivatives Accompanying with Transposition of the Triple Bond2014

    • Author(s)
      張田原,高野淳,西山侑太郎,前川博史
    • Organizer
      第67回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      慶應義塾大学(神奈川県横浜市)
    • Year and Date
      2014-05-17
    • Related Report
      2014 Research-status Report
  • [Presentation] 芳香族アルデヒド,エステルとトリフルオロ酢酸エチルのマグネシウム金属還元カップリング反応

    • Author(s)
      前川博史,工藤将士,西山侑太郎,安部光弘,清水一行,ワンノルマヤニ,木原 伸
    • Organizer
      第37回有機電子移動化学討論会
    • Place of Presentation
      岡山大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Novel Synthesis of Multi-functionalized Allenes by Mg-promoted Reductive Silylation of Phenylacetylene Derivatives

    • Author(s)
      Atsushi Takano, Masamitsu Watanabe, Hirofumi Maekawa
    • Organizer
      11th international Symposium of Organic Reactions
    • Place of Presentation
      台北,台湾
    • Related Report
      2013 Research-status Report
    • Invited
  • [Presentation] Mg-Promoted Reductive Trifluoroacetylation of Vinylpyridines

    • Author(s)
      西山侑太郎,前川博史
    • Organizer
      The 4th German-Japanese Symposium on Electrosynthesis
    • Place of Presentation
      京都大学
    • Related Report
      2013 Research-status Report
  • [Presentation] マグネシウム金属還元法によるベンゾイルアセチレン類のシリル化反応

    • Author(s)
      内山遼太郎,高野 淳,西山侑太郎,前川博史
    • Organizer
      日本化学会第94回春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Book] PEL有機化学2015

    • Author(s)
      粳間由幸編著
    • Total Pages
      214
    • Publisher
      実教出版
    • Related Report
      2015 Annual Research Report
  • [Book] 第2版有機合成実験法ガイドブック2015

    • Author(s)
      有機合成化学協会編
    • Total Pages
      1166
    • Publisher
      丸善出版
    • Related Report
      2015 Annual Research Report
  • [Book] Encyclopedia of Applied Electrochemistry2014

    • Author(s)
      K. Ohta, G. Kreysa, R. F. Savinell, eds. H. Maekawa
    • Total Pages
      2169
    • Publisher
      Springer Science
    • Related Report
      2014 Research-status Report
  • [Remarks] 長岡技術科学大学研究者総覧

    • URL

      http://souran.nagaokaut.ac.jp/view?l=ja&u=164&i=j30&sm=name&sl=ja&sp=1

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
  • [Remarks] 研究者詳細

    • URL

      http://souran.nagaokaut.ac.jp/view?l=ja&u=164&i=j30&sm=name&sl=ja&sp=1

    • Related Report
      2013 Research-status Report

URL: 

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

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