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Catalytic regioselective hetero-functionalizaiton of arenes

Research Project

Project/Area Number 15K17821
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Murakami Kei  名古屋大学, トランスフォーマティブ生命分子研究所(WPI), 准教授 (90732058)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,290,000 (Direct Cost: ¥3,300,000、Indirect Cost: ¥990,000)
Fiscal Year 2016: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords芳香族アミノ化 / 銅触媒 / ルテニウム触媒 / スルホンイミド / 光触媒 / 窒素ラジカル / アミノ化 / 遷移金属触媒 / 二座配位子
Outline of Final Research Achievements

Functional molecules such as natural products, pharmaceuticals, and organic materials are indispensable. Arylamines are one of the most important structures of these functional molecules. However, direct synthesis of arylamine through C-H functionalization of arenes is difficult. In this research, development of new synthesis of arylamines are studied. At the starting point, we elucidated the mechanism of copper-catalyzed arylamine (arylimide) synthesis by using DFT calculations. Based on this finding, we have developed a new arylamine (arylimide) synthesis using photocatalyst. The scope of the reaction is wide enough to cover various polyaromatic hydrocarbons as well as heteroarenes.

Report

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

    (43 results)

All 2017 2016 2015 Other

All Journal Article (5 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 5 results,  Acknowledgement Compliant: 5 results,  Open Access: 1 results) Presentation (34 results) (of which Int'l Joint Research: 5 results,  Invited: 4 results) Remarks (4 results)

  • [Journal Article] Cu-Catalyzed aromatic C-H imidation with N-fluorobenzenesulfonimide: mechanistic details and predictive models2017

    • Author(s)
      Brandon E. Haines, Takahiro Kawakami, Keiko Kuwata, Kei Murakami, Kenichiro Itami, Djamaladdin G. Musaev
    • Journal Title

      Chemical Science

      Volume: 8 Issue: 2 Pages: 988-1001

    • DOI

      10.1039/c6sc04145k

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Catalytic Dehydrogenative C-H Imidation of Arenes Enabled by Photo-generated Hole Donation to Sulfonimide2017

    • Author(s)
      Eri Ito, Tomohiro Fukushima, Takahiro Kawakami, Kei Murakami, Kenichiro Itami
    • Journal Title

      Chem

      Volume: 2 Issue: 3 Pages: 383-392

    • DOI

      10.1016/j.chempr.2017.02.006

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regiodivergent Cross-Dehydrogenative Coupling of Pyridines and Benzoxazoles: Discovery of Organic Halides as Regio-Switching Oxidants2016

    • Author(s)
      Shuya Yamada, Kei Murakami, Kenichiro Itami
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 10 Pages: 2415-2418

    • DOI

      10.1021/acs.orglett.6b00932

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-catalyzed C-H Arylation of Pyridines with Aryl Triflates2016

    • Author(s)
      Jiao Jiao, Kei Murakami, Kenichiro Itami
    • Journal Title

      Chemistry Letters

      Volume: NA Issue: 5 Pages: 529-531

    • DOI

      10.1246/cl.160133

    • NAID

      130005150484

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Catalytic Methods for Aromatic C-H Amination: An Ideal Strategy for Nitrogen-Based Functional Molecules2016

    • Author(s)
      Jiao Jiao, Kei Murakami, Kenichiro Itami
    • Journal Title

      ACS catalysis

      Volume: 6 Issue: 2 Pages: 610-633

    • DOI

      10.1021/acscatal.5b02417

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 遷移金属触媒を用いる分子の構築と修飾2017

    • Author(s)
      村上慧
    • Organizer
      2nd Organic Chemistry Symposium
    • Place of Presentation
      京都
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] Palladium-catalyzed C2-selective Dimerization of Pyridines2017

    • Author(s)
      山田柊哉・金田岳志・村上慧・伊丹健一郎
    • Organizer
      グリーン自然科学国際教育研究プログラム IGER 2016年度年次報告会
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development of C-H imidation for plant biology2017

    • Author(s)
      Eri Ito, Shimpei Inoue, Yosuke Toda, Takahiro Kawakami, Mina Narouz, Kei Murakami, Toshinori Kinoshita, Kenichiro Itami
    • Organizer
      The 3rd CSRS-ITbM Joint Workshop
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
  • [Presentation] パラジウム触媒を用いる多環芳香族炭化水素の新規合成法の開発2017

    • Author(s)
      古賀 義人・金田 岳志・齋藤 雄太朗・村上 慧・伊丹 健一郎
    • Organizer
      日本化学会 第97春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2016 Annual Research Report
  • [Presentation] ルテニウム触媒を用いた光駆動型芳香族C-Hイミド化反応2017

    • Author(s)
      伊藤江里・福島知宏・川上貴大・村上慧・伊丹健一郎
    • Organizer
      日本化学会 第97春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2016 Annual Research Report
  • [Presentation] パラジウム触媒を用いたピリジン2位選択的二量化反応の開発2017

    • Author(s)
      山田柊哉・金田岳志・村上慧・伊丹健一郎
    • Organizer
      日本化学会 第97春季年会
    • Place of Presentation
      神奈川
    • Related Report
      2016 Annual Research Report
  • [Presentation] 学際研究が加速する新しい反応化学2016

    • Author(s)
      村上慧
    • Organizer
      白眉秋合宿
    • Place of Presentation
      京都
    • Year and Date
      2016-12-09
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 「本当に」ほしいものを作る反応方法論の開発2016

    • Author(s)
      村上慧
    • Organizer
      第十一回有機元素化学セミナー
    • Place of Presentation
      京都
    • Year and Date
      2016-06-03
    • Related Report
      2016 Annual Research Report
    • Invited
  • [Presentation] 銅触媒を用いた芳香族C-Hイミド化反応:反応機構に基づく配位子設計2016

    • Author(s)
      川上貴大・村上慧・伊丹健一郎
    • Organizer
      日本化学会 第96春季年会
    • Place of Presentation
      京都
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] パラジウム触媒によるピリジンとアゾールの直接カップリング:酸化剤による位置選択性の制御2016

    • Author(s)
      山田柊哉・村上慧・伊丹健一郎
    • Organizer
      日本化学会 第96春季年会
    • Place of Presentation
      京都
    • Year and Date
      2016-03-25
    • Related Report
      2015 Research-status Report
  • [Presentation] Development of new C-H imidation for biological application2016

    • Author(s)
      村上慧
    • Organizer
      2016ITbM-IoC Joint Workshop on Biomolecules and Materials
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Palladium-catalyzed direct coupling of pyridine and benzoxazole: Oxidant-controlled regiodivergency2016

    • Author(s)
      Shuya Yamada, Kei Murakami, Kenichiro Itami
    • Organizer
      The 20th International Symposium on Homogeneous Catalysis (ISHC20)
    • Place of Presentation
      京都
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Development of New Palladium-Catalyzed Reaction of Haloarenes2016

    • Author(s)
      Yoshito Koga, Takeshi Kaneda, Yutaro Saito, Kei Murakami, Kenichiro Itami
    • Organizer
      2016 International C-H Functionalization Workshop
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Palladium-catalyzed Dimerization of Pyridines2016

    • Author(s)
      山田柊哉・金田岳志・村上慧・伊丹健一郎
    • Organizer
      第2回ITbM/IGER Chemistry Workshop
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
  • [Presentation] Catalytic Dehydrogenative C-H Imitation of Arenes Enabled by Photo-Generated Hole Donation to Sulfonimide2016

    • Author(s)
      伊藤江里・福島知宏・川上貴大・村上慧・伊丹健一郎
    • Organizer
      IGER/ITbM Chemistry Workshop 2016
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
  • [Presentation] 芳香族ハロゲン化物からベンザインへの効率的変換法の開発2016

    • Author(s)
      古賀義人・金田岳志・齋藤雄太朗・村上慧・伊丹健一郎
    • Organizer
      IGER/ITbM Chemistry Workshop 2016
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
  • [Presentation] Copper-Catalyzed Synthesis of α-Fluoroimines from Alkynes2016

    • Author(s)
      Shu Jan Yip, Tetsushi Yoshidomi, Kei Murakami, Kenichiro Itami
    • Organizer
      IGER/ITbM Chemistry Workshop 2016
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
  • [Presentation] 芳香族ハロゲン化物からベンザインへの効率的変換法の開発2016

    • Author(s)
      古賀義人、金田岳志、齋藤雄太朗、村上慧、伊丹健一郎
    • Organizer
      第34回メディシナルケミストリーシンポジウム
    • Place of Presentation
      つくば
    • Related Report
      2016 Annual Research Report
  • [Presentation] パラジウム触媒によるピリジンとベンゾオキサゾールの直接カップリング:酸化剤による位置選択性の制御2016

    • Author(s)
      山田柊哉、村上慧、伊丹健一郎
    • Organizer
      第34回メディシナルケミストリーシンポジウム
    • Place of Presentation
      つくば
    • Related Report
      2016 Annual Research Report
  • [Presentation] 新たな触媒的イミド化反応の開発2016

    • Author(s)
      伊藤江里、福島知宏、川上貴大、村上慧、伊丹健一郎
    • Organizer
      第6回CSJ化学フェスタ
    • Place of Presentation
      東京
    • Related Report
      2016 Annual Research Report
  • [Presentation] 芳香族ハロゲン化物からベンザインへの効率的変換2016

    • Author(s)
      古賀義人・金田岳志・齋藤雄太朗・村上慧・伊丹健一郎
    • Organizer
      第6回CSJ化学フェスタ
    • Place of Presentation
      東京
    • Related Report
      2016 Annual Research Report
  • [Presentation] Palladium-Catalyzed Direct Coupling of Pyridine and Benzoxazole: Oxidant-Controlled Regiodivergency2016

    • Author(s)
      Shuya Yamada, Kei Murakami, Kenichiro Itami
    • Organizer
      第63回有機金属化学討論会
    • Place of Presentation
      東京
    • Related Report
      2016 Annual Research Report
  • [Presentation] 芳香族ハロゲン化物からベンザインへの効率的変換2016

    • Author(s)
      古賀義人・金田岳志・齋藤雄太朗・村上慧・伊丹健一郎
    • Organizer
      第33回有機合成化学セミナー
    • Place of Presentation
      北海道
    • Related Report
      2016 Annual Research Report
  • [Presentation] パラジウム触媒によるピリジンとベンゾオキサゾールの直接カップリング:酸化剤による位置選択性の制御2016

    • Author(s)
      山田柊哉・村上慧・伊丹健一郎
    • Organizer
      第33回有機合成化学セミナー
    • Place of Presentation
      北海道
    • Related Report
      2016 Annual Research Report
  • [Presentation] 有機分子に窒素原子を導入し、画期的な機能性分子を創る2016

    • Author(s)
      伊藤江里・川上貴大・村上慧・伊丹健一郎
    • Organizer
      名古屋大学若手女性研究者サイエンスフォーラム
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development of new palladium-catalyzed reaction of haloarenes2016

    • Author(s)
      Yoshito Koga, Takeshi Kaneda, Yutaro Saito, Kei Murakami, Kenichiro Itami
    • Organizer
      統合物質創製化学研究推進機構 キックオフシンポジウム
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development of new C-H aromatic imidation reaction2016

    • Author(s)
      Eri Ito, Takahiro Kawakami, Kei Murakami, Kenichiro Itami
    • Organizer
      統合物質創製化学研究推進機構 キックオフシンポジウム
    • Place of Presentation
      名古屋
    • Related Report
      2016 Annual Research Report
  • [Presentation] 新たな触媒的イミド化反応の開発2016

    • Author(s)
      伊藤江里、川上貴大、村上慧、伊丹健一郎
    • Organizer
      第十一回有機元素化学セミナー
    • Place of Presentation
      京都
    • Related Report
      2016 Annual Research Report
  • [Presentation] Development of New Palladium-Catalyzed Reaction of Haloarenes2016

    • Author(s)
      古賀義人、金田岳志、齋藤雄太朗、村上慧、伊丹健一郎
    • Organizer
      第十一回有機元素化学セミナー
    • Place of Presentation
      京都
    • Related Report
      2016 Annual Research Report
  • [Presentation] Site-selective functionalization of pyridine2016

    • Author(s)
      山田柊哉・村上慧・伊丹健一郎
    • Organizer
      第十回有機元素化学セミナー
    • Place of Presentation
      京都
    • Related Report
      2016 Annual Research Report 2015 Research-status Report
  • [Presentation] Development of transition-metal-catalyzed imidation for adding handles to functional molecules2015

    • Author(s)
      Kei Murakami, Takahiro Kawakami, Kenichiro Itami
    • Organizer
      Pacifichem 2015 meeting
    • Place of Presentation
      Honolulu USA
    • Year and Date
      2015-12-15
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] Catalytic C-H Imidation of Aromatic Core of Functional Molecules2015

    • Author(s)
      Takahiro Kawakami, Kei Murakami, Kenichiro Itami
    • Organizer
      The 13th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-13)
    • Place of Presentation
      Kyoto Japan
    • Year and Date
      2015-11-11
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] 機能分子の芳香環コアの触媒的C-Hイミド化2015

    • Author(s)
      村上 慧・川上貴大・伊丹健一郎
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2015-09-07
    • Related Report
      2015 Research-status Report
  • [Presentation] Ligand-accelerated Cu-catalyzed C-H imidation of arenes2015

    • Author(s)
      川上貴大・村上慧・伊丹健一郎
    • Organizer
      第十回有機元素化学セミナー
    • Place of Presentation
      京都
    • Year and Date
      2015-06-08
    • Related Report
      2015 Research-status Report
  • [Remarks] Catalytic Dehydrogenative C-H Imidation of Arenes

    • URL

      http://synth.chem.nagoya-u.ac.jp/wordpress/publication/dehydrogenative-imidation

    • Related Report
      2016 Annual Research Report
  • [Remarks] Mechanistic details of C-H imidation

    • URL

      http://synth.chem.nagoya-u.ac.jp/wordpress/publication/imidation-mechanism

    • Related Report
      2016 Annual Research Report
  • [Remarks] Regiodivergent Coupling of Pyridines

    • URL

      http://synth.chem.nagoya-u.ac.jp/wordpress/publication/regiodivergent-cross-dehydrogenative-coupling-of-pyridines-and-benzoxazoles-discovery-of-organic-halides-as-regio-switching-oxidants

    • Related Report
      2016 Annual Research Report
  • [Remarks] 光触媒が可能にする新規C-H/N-Hカップリング

    • URL

      http://www.chem-station.com/blog/2017/03/c-hn-h.html

    • Related Report
      2016 Annual Research Report

URL: 

Published: 2015-04-16   Modified: 2018-03-22  

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