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Studies on Alkylation Reactions of Arenes without Ortho-directing Groups

Research Project

Project/Area Number 25708006
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypePartial Multi-year Fund
Research Field Organic chemistry
Research InstitutionKyoto University

Principal Investigator

Nakao Yoshiaki  京都大学, 工学研究科, 教授 (60346088)

Project Period (FY) 2013-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥25,350,000 (Direct Cost: ¥19,500,000、Indirect Cost: ¥5,850,000)
Fiscal Year 2016: ¥8,320,000 (Direct Cost: ¥6,400,000、Indirect Cost: ¥1,920,000)
Fiscal Year 2015: ¥8,320,000 (Direct Cost: ¥6,400,000、Indirect Cost: ¥1,920,000)
Fiscal Year 2014: ¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2013: ¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Keywordsベンゼン / アルケン / アルキル化 / 遷移金属 / ニッケル / 協働触媒 / ルイス酸 / アルミニウム / C-H 官能基化 / C-H官能基化
Outline of Final Research Achievements

Alkylation reactions of arenes without ortho-directing groups have been investigated using alkenes as alkylating agents. First, we have found that nickel complexes bearing N-heterocyclic carbenes catalyze the reaction of benzene with 1-alkenes with unprecedentedly high linear selectivity to give linear alkylbenzenes. We have also shown that the nickel complexes in combination with aluminum-based Lewis acid cooperatively catalyze para- or meta-selective alkylation of benzenes bearing heteroatom-containing substituents such as aromatic carbonyl compounds, aromatic sulfonyl compounds, and anilides.

Report

(6 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • 2015 Annual Research Report
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (34 results)

All 2018 2017 2016 2015 2014 Other

All Int'l Joint Research (1 results) Journal Article (3 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results) Presentation (30 results) (of which Int'l Joint Research: 10 results,  Invited: 20 results)

  • [Int'l Joint Research] University of California, Berkeley(米国)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Site-Selective Linear Alkylation of Anilides by Cooperative Nickel/Aluminum Catalysis2017

    • Author(s)
      Okumura Shogo、Komine Takuya、Shigeki Erika、Semba Kazuhiko、Nakao Yoshiaki
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 57 Issue: 4 Pages: 929-932

    • DOI

      10.1002/anie.201710520

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] para-Selective Alkylation of Sulfonylarenes by Cooperative Nickel/Aluminum Catalysis2017

    • Author(s)
      Shogo Okumura, Yoshiaki Nakao
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 3 Pages: 584-587

    • DOI

      10.1021/acs.orglett.6b03741

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] para-Selective Alkylation of Benzamides and Aromatic Ketones by Cooperative Nickel/Aluminum Catalysis2016

    • Author(s)
      Shogo Okumura, Shuwei Tang, Teruhiko Saito, Kazuhiko Semba, Shigeyoshi Sakaki, Yoshiaki Nakao
    • Journal Title

      Journal of the American Chemical Society

      Volume: 138 Issue: 44 Pages: 14699-14704

    • DOI

      10.1021/jacs.6b08767

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Presentation] 協働金属触媒による有機合成反応2018

    • Author(s)
      中尾佳亮
    • Organizer
      東北大学大学院薬学研究科セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 協働金属触媒による有機合成反応2017

    • Author(s)
      中尾佳亮
    • Organizer
      パイスター分子制御による未来型物質変換研究拠点 2017年度公開シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 協働金属触媒による有機合成反応2017

    • Author(s)
      中尾佳亮
    • Organizer
      第6回 IoLコロキウム 特別講演会
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] C-H Functionalization by Cooperative Metal Catalysis2017

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      1st Singapore Japan Germany Trilateral Symposium on Precision Synthesis&Catalysis
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Nickel Catalysis for Hydroarylation and Related Reactions2017

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      Symposium on Nickel and Related Chemistry
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Cooperative Metal Catalysis for Efficient Organic Synthesis2017

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      1st International Symposium on Catalysis for Sustainable Chemical Synthesis Joint Symposium of FRIAS/Nagoya IAR,
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 協働金属触媒による有機合成反応2017

    • Author(s)
      中尾佳亮
    • Organizer
      第34回有機合成化学セミナー
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] C-H Functionalization by Cooperative Catalysis2017

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      Nordic/Kyoto OMCOS 2017
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Cooperative Metal Catalysis for Efficient Organic Synthesis2017

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      SUS Tech Chemical Sciences Lectureship
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] ニッケル/アルミニウム協働触媒によるアルケンを用いた芳香族カルボニルおよびスルホニル化合物のパラ位選択的アルキル化反応2016

    • Author(s)
      奥村省吾, Tang Shuwei, 齊藤輝彦, 仙波一彦, 榊茂好, 中尾佳亮
    • 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] 協働金属触媒による有機合成反応2016

    • Author(s)
      中尾佳亮
    • Organizer
      ITbM/IGER Chemistry Workshop
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 協働金属触媒による有機合成反応2016

    • Author(s)
      中尾佳亮
    • Organizer
      早稲田大学理工学術院
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 協働金属触媒による有機合成反応2016

    • Author(s)
      中尾佳亮
    • Organizer
      平成28年度 後期(秋季)有機合成化学講習会
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Cooperative Metal Catalysis for Efficient Organic Synthesis2016

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      9th Asian-European Symposium on Metal-Mediated Efficient Organic Synthesis
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Cooperative Metal Catalysis for Efficient Organic Synthesis2016

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      The 3rd International Conference on Organometallics and Catalysis
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Ni-Catalyzed Linear-Selective Alkylation of Benzene with Olefins2015

    • Author(s)
      Akito Ohgi, Teruhiko Saito, Kazuhiko Semba, Yoshiaki Nakao, John F. Hartwig
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto
    • Year and Date
      2015-11-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] para-Selective Alkylation of Benzamides by Cooperative Nickel/Aluminum Catalysis2015

    • Author(s)
      Shogo Okumura, Shuwei Tang, Teruhiko Saito, Kazuhiko Semba, Shigeyuki Sakaki, Yoshiaki Nakao
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      Kyoto
    • Year and Date
      2015-11-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ニッケル/アルミニウム協働触媒による安息香酸アミドのパラ位選択的アルキル化反応2015

    • Author(s)
      奥村省吾, Shuwei Tang, 仙波一彦, 齊藤輝彦, 榊茂好, 中尾佳亮
    • Organizer
      第31回若手化学者のための化学道場
    • Place of Presentation
      淡路夢舞台国際会議
    • Year and Date
      2015-08-26
    • Related Report
      2015 Annual Research Report
  • [Presentation] Ni-catalyzed Linear-selective Alkylation of Benzene with Olefins2015

    • Author(s)
      Akito Ohgi, Teruhiko Saito, Kazuhiko Semba, Yoshiaki Nakao, John F. Hartwi
    • Organizer
      The 18th Organometallic Chemistry Directed Towards Organic Synthesis IUPAC International Symposium
    • Place of Presentation
      Sitges
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] C-C Bond Forming Reactions by Cooperative Metal Catalysis2015

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      日本化学会第95春季年会 テトラへドロン受賞シンポジウム
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ニッケル触媒によるベンゼンの直鎖選択的アルキル化反応2015

    • Author(s)
      大木暁登, 齊藤輝彦, 仙波一彦, 中尾佳亮
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] ニッケル/アルミニウム協働触媒による安息香酸アミドのパラ位選択的アルキル化反応2015

    • Author(s)
      奥村省吾, 齊藤輝彦, 仙波一彦, 中尾佳亮
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学
    • Year and Date
      2015-03-26
    • Related Report
      2014 Annual Research Report
  • [Presentation] 協働金属触媒による炭素ー炭素結合形成反応2014

    • Author(s)
      中尾佳亮
    • Organizer
      第68回有機合成化学協会関東支部シンポジウム(新潟シンポジウム)
    • Place of Presentation
      新潟大学
    • Year and Date
      2014-11-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Arene Alkylation by Nickel Catalysis2014

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      Progress in Catalytic C-H Activation over the Past Twenty Years (The Murai Symposium)
    • Place of Presentation
      Nara
    • Year and Date
      2014-10-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Ni/Al協働触媒によるアニリド類及び安息香酸アミド類のアルキル化反応2014

    • Author(s)
      奥村省吾, 小峰卓也, 仙波一彦, 中尾佳亮
    • Organizer
      第4回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2014-10-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] Ni/Al協働触媒によるアニリド類及び安息香酸アミド類のアルキル化反応2014

    • Author(s)
      奥村省吾, 小峰卓也, 仙波一彦, 中尾佳亮
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学
    • Year and Date
      2014-09-25
    • Related Report
      2014 Annual Research Report
  • [Presentation] 協働金属触媒による炭素ー炭素結合形成反応2014

    • Author(s)
      中尾佳亮
    • Organizer
      第47回有機金属若手の会 夏の学校
    • Place of Presentation
      休暇村大久野島
    • Year and Date
      2014-09-03
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ニッケル触媒によるベンゼンの直鎖選択的アルキル化反応2014

    • Author(s)
      大木暁登, 齊藤輝彦, 仙波一彦, 中尾佳亮
    • Organizer
      第47回有機金属若手の会 夏の学校
    • Place of Presentation
      休暇村大久野島
    • Year and Date
      2014-09-02
    • Related Report
      2014 Annual Research Report
  • [Presentation] C-C Bond Forming Reactions by Cooperative Metal Catalysis2014

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      ICOMC2014 Post-Symposium in Okayama
    • Place of Presentation
      Okayama
    • Year and Date
      2014-07-20
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] C-C Bond Forming Reactions by Cooperative Metal Catalysis2014

    • Author(s)
      Yoshiaki Nakao
    • Organizer
      The 19th International Symposium on Homogeneous Catalysis (ISHC-19)
    • Place of Presentation
      Ottawa
    • Year and Date
      2014-07-09
    • Related Report
      2014 Annual Research Report
    • Invited

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Published: 2013-05-21   Modified: 2022-01-27  

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