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Develop bi-functional catalysts for innovative cross-coupling reaction

Research Project

Project/Area Number 25708005
Research Category

Grant-in-Aid for Young Scientists (A)

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

Principal Investigator

Yamaguchi Junichiro  名古屋大学, 理学(系)研究科(研究院), 准教授 (00529026)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥23,140,000 (Direct Cost: ¥17,800,000、Indirect Cost: ¥5,340,000)
Fiscal Year 2015: ¥2,860,000 (Direct Cost: ¥2,200,000、Indirect Cost: ¥660,000)
Fiscal Year 2014: ¥5,980,000 (Direct Cost: ¥4,600,000、Indirect Cost: ¥1,380,000)
Fiscal Year 2013: ¥14,300,000 (Direct Cost: ¥11,000,000、Indirect Cost: ¥3,300,000)
Keywordsカップリング反応 / 分子結合活性化 / 遷移金属触媒反応 / 天然物合成 / 分子活性化 / 触媒 / パラジウム / ニッケル / 合成化学 / 触媒化学
Outline of Final Research Achievements

The C-H coupling method (C-H/C-X type coupling) requires dramatic advantage compared with a classical cross-coupling method (C-M/C-X type coupling) from substrate scope, reactivity and utility the point of view. Meanwhile, the applicant have also already been reported C-H/C-O coupling of azoles with phenol/enol derivatives and decarbonylative C-H coupling of azoles with phenyl esters /alkenyl esters, that are formally enable to activate both C-H bond and relatively stable C-Y bonds (Y = OR, CO2R) at the same time. We believe that this kind of multi-bonds (ethers, esters, nitriles, and amides) functionalization to create C-C bonds is entirely different from classical cross-coupling method and is to be next-generation cross-coupling method as well as one of the molecular technologies. Based on the motivation, we developed such a coupling methods and an enabled catalysts. We have achieved rapid syntheses of useful molecules and natural products.

Report

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

    (55 results)

All 2016 2015 2014 2013 Other

All Int'l Joint Research (2 results) Journal Article (15 results) (of which Int'l Joint Research: 3 results,  Peer Reviewed: 15 results,  Acknowledgement Compliant: 10 results,  Open Access: 3 results) Presentation (26 results) (of which Int'l Joint Research: 7 results,  Invited: 26 results) Book (2 results) Remarks (5 results) Patent(Industrial Property Rights) (5 results)

  • [Int'l Joint Research] エモリー大学(米国)

    • Related Report
      2015 Annual Research Report
  • [Int'l Joint Research] スクリプス研究所(米国)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Synthesis of Triarylpyridines in Thiopeptide Antibiotics by Using a C-H Arylation/Ring-Transformation Strategy2016

    • Author(s)
      Kazuma Amaike, Kenichiro Itami, and Junichiro Yamaguchi
    • Journal Title

      Chemistry - A European Journal

      Volume: 22 Issue: 13 Pages: 4384-4388

    • DOI

      10.1002/chem.201600351

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] C-H Activation Generates Period-Shortening Moleculaes That Target Cryptochrome in the Mammalian Circadian Clock.2015

    • Author(s)
      Oshima T, Yamanaka I, Kumar A, Yamaguchi J, Nishiwaki-Okawa T, Muto K, Kawamura R, Hirota T, Yagita K, Irie S, Kay SA, Yoshimura T, Itami K.
    • Journal Title

      Angew Chem Int Ed

      Volume: 54 Issue: 24 Pages: 7193-7197

    • DOI

      10.1002/anie.201502942

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Decarbonylative Organoboron Cross-coupling of Esters by Nickel Catalysis2015

    • Author(s)
      Kei Muto, Junichiro Yamaguchi, Djamaladdin G. Musaev, and Kenichiro Itami
    • Journal Title

      Nature Communication

      Volume: 6 Issue: 1 Pages: 7508-7508

    • DOI

      10.1038/ncomms8508

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] C-H Arylation and Alkenylation of Imidazoles by Nickel Catalysis: Solvent accelerated Imidazole C-H Activation2015

    • Author(s)
      Kei Muto, Taito Hatakeyama, Junichiro Yamaguchi, Kenichiro Itami
    • Journal Title

      Chemical Science

      Volume: 6 Issue: 12 Pages: 6792-6798

    • DOI

      10.1039/c5sc02942b

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Open Access / Int'l Joint Research / Acknowledgement Compliant
  • [Journal Article] Stereodivergent Synthesis of Arylcyclopropylamines bySequential C-H Borylation and Suzuki-Miyaura Coupling2015

    • Author(s)
      宮村伸、荒木美沙保、鈴木 孝禎、山口潤一郎、伊丹健一郎
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 2015 Issue: 3 Pages: 846-851

    • DOI

      10.1002/anie.201409186

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Ni-Catalyzed α-Arylation of Esters and Amides with Phenol Derivatives2015

    • Author(s)
      Koch Eva, 瀧瀬瞭介、武藤慶、山口潤一郎、伊丹健一郎
    • Journal Title

      Chem Comm

      Volume: 51 Issue: 5 Pages: 855-857

    • DOI

      10.1039/c4cc08426h

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Concise Syntheses of Dictyodendrins A and F by a Sequential C-H Functionalization Strategy2015

    • Author(s)
      Atsushi D. Yamaguchi, Kathryn M. Chepiga, Junichiro Yamaguchi, Kenichiro Itami, Huw M. L. Davies
    • Journal Title

      Journal of the American Chemical Society

      Volume: 137 Issue: 2 Pages: 644-647

    • DOI

      10.1021/ja512059d

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Nickel-Catalyzed α-Arylation of Ketones with Phenol Derivatives2014

    • Author(s)
      Ryosuke Takise, Kei Muto, Junichiro Yamaguchi, Kenichiro Itami
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 53 Issue: 26 Pages: 6791-6794

    • DOI

      10.1002/anie.201403823

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Regioselective Allylic C-H Oxidation of Terminal Alkenes with Pd/sulfoxide-oxazoline Catalyst2014

    • Author(s)
      近藤寛起、Yu Feng、山口潤一郎、Liu Guosheng、伊丹健一郎
    • Journal Title

      Org. Lett

      Volume: 16 Issue: 16 Pages: 4212-4215

    • DOI

      10.1021/ol5019135

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] β-Selective C-H Arylation of Pyrroles Leading to Concise Syntheses of Lamellarins C and I2014

    • Author(s)
      Kirika Ueda, Kazuma Amaike, Richard M. Maceiczyk, Kenichiro Itami, and Junichiro Yamaguch
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 38 Pages: 13226-13232

    • DOI

      10.1021/ja508449y

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Key Mechanistic Features of Ni-Catalyzed C-H/C-O Biaryl Coupling of Azoles and Naphthalen-2-yl Pivalates2014

    • Author(s)
      Huiying Xu, Kei Muto, Junichiro Yamaguchi, Cunyuan Zhao, Kenichiro Itami, Djamaladdin G. Musaev
    • Journal Title

      Journal of the American Chemical Society

      Volume: 136 Issue: 42 Pages: 14834-14844

    • DOI

      10.1021/ja5071174

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Programmed Synthesis of Arylthiazoles through Sequential C-H Couplings2014

    • Author(s)
      谷聡、上原貴大、山口純一郎、伊丹健一郎
    • Journal Title

      Chem. Sci

      Volume: 5 Issue: 1 Pages: 123-135

    • DOI

      10.1039/c3sc52199k

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Aromatic C-H Coupling with Hindered Arylboronic Acids by Pd/Fe Dual Catalysts2013

    • Author(s)
      山口和也、近藤寛起、山口潤一郎、伊丹健一郎
    • Journal Title

      Chem. Sci

      Volume: 4 Issue: 9 Pages: 3753-3757

    • DOI

      10.1039/c3sc51206a

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] C-H Alkenylation of Azoles with Enols and Esters by Nickel Catalysis2013

    • Author(s)
      Meng Lingkui, 鎌田祐子, 武藤慶, 山口潤一郎, 伊丹健一郎
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 38 Pages: 10048-10051

    • DOI

      10.1002/anie.201304492

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Isolation, Structure, and Reactivity of an Arylnickel (II) Pivatate Complex in Catalytic C-H/C-O Biaryl Coupling2013

    • Author(s)
      武藤慶, 山口潤一郎, Lei Aiwen, 伊丹健一郎
    • Journal Title

      Journal of the American Chemical Society

      Volume: 135 Issue: 44 Pages: 16384-16387

    • DOI

      10.1021/ja409803x

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] 自在な分子構築法の探究とその活用2016

    • Author(s)
      山口潤一郎
    • Organizer
      早稲田大学
    • Place of Presentation
      早稲田大学
    • Year and Date
      2016-03-18
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A C-H Arylation/Ring Transformation Approach: Synthesis of Polyarylated Arenes and Natural Products2015

    • Author(s)
      山口潤一郎
    • Organizer
      Peking University Shenzhen Graduate School
    • Place of Presentation
      Peking University Shenzhen Graduate School
    • Year and Date
      2015-09-11
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A C-H Arylation/Ring Transformation Approach: Synthesis of Polyarylated Arenes and Natural Products2015

    • Author(s)
      山口潤一郎
    • Organizer
      South China University of Technology
    • Place of Presentation
      South China University of Technology
    • Year and Date
      2015-09-10
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A C-H Arylation/Ring Transformation Approach: Synthesis of Polyarylated Arenes and Natural Products2015

    • Author(s)
      山口潤一郎
    • Organizer
      South University of Science and Technology of China
    • Place of Presentation
      South University of Science and Technology of China
    • Year and Date
      2015-09-10
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A C-H Arylation/Ring Transformation Approach: Synthesis of Polyarylated Arenes and Natural Products2015

    • Author(s)
      山口潤一郎
    • Organizer
      Hunan University
    • Place of Presentation
      Hunan University
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A C-H Arylation/Ring Transformation Approach: Synthesis of Polyarylated Arenes and Natural Products2015

    • Author(s)
      山口潤一郎
    • Organizer
      China Normal University
    • Place of Presentation
      China Normal University
    • Year and Date
      2015-09-08
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] A C-H Arylation/Ring Transformation Approach: Synthesis of Polyarylated Arenes and Natural Products2015

    • Author(s)
      山口潤一郎
    • Organizer
      Wuhan University
    • Place of Presentation
      Wuhan University
    • Year and Date
      2015-09-07
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 新規芳香環連結法の開発と応用2015

    • Author(s)
      山口潤一郎
    • Organizer
      早稲田大学応化セミナー
    • Place of Presentation
      早稲田大学、東京
    • Year and Date
      2015-08-02
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 新規カップリング反応/環変換反応による多アリール化芳香族化合物の合成2015

    • Author(s)
      山口潤一郎
    • Organizer
      高分子同友会
    • Place of Presentation
      高分子同友会、東京
    • Year and Date
      2015-07-23
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 分子レベルのものづくりを究める2015

    • Author(s)
      山口潤一郎
    • Organizer
      中央大学講演会
    • Place of Presentation
      中央大学、東京
    • Year and Date
      2015-07-18
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] 芳香環直接連結反応の開発とその展開2015

    • Author(s)
      山口潤一郎
    • Organizer
      持田製薬特別講演会
    • Place of Presentation
      持田製薬、神奈川
    • Year and Date
      2015-04-15
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] A C-H Arylation/Ring Transformation Approach: Synthesis of Polyarylated Arenes and Natural Products2015

    • Author(s)
      山口潤一郎
    • Organizer
      第5 回日中若手化学者フォーラム
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-27
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 芳香環直接連結反応の開発・応用・深化2015

    • Author(s)
      山口潤一郎
    • Organizer
      住友化学特別講演会
    • Place of Presentation
      大阪
    • Year and Date
      2015-02-23
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Toward an Ideal Synthesis of Bioactive Molecules Through Direct Arene Assembling Reactions2015

    • Author(s)
      山口潤一郎
    • Organizer
      NTU Seminar
    • Place of Presentation
      シンガポール
    • Year and Date
      2015-02-05
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Toward an Ideal Synthesis of Bioactive Molecules Through Direct Arene Assembling Reactions2015

    • Author(s)
      山口潤一郎
    • Organizer
      NUS Seminar
    • Place of Presentation
      シンガポール
    • Year and Date
      2015-02-02
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Ni 触媒を用いた脱エステル型カップリング反応2015

    • Author(s)
      山口 潤一郎
    • Organizer
      第8回分子活性化公開シンポジウム
    • Place of Presentation
      大阪大学
    • Year and Date
      2015-01-23
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] Programmed Synthesis of Hexaarylbenzenes2014

    • Author(s)
      山口 潤一郎
    • Organizer
      第5回国際若手シンポジウム
    • Place of Presentation
      熊本
    • Year and Date
      2014-12-19
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 分子モデルのように分子を繋げる触媒の開発を目指して」2014

    • Author(s)
      山口 潤一郎
    • Organizer
      熊本大学自然科学研究コア特別講演会
    • Place of Presentation
      熊本大学
    • Year and Date
      2014-12-18
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] ニッケル触媒によるヘテロビアリール合成法の開発と応用2014

    • Author(s)
      山口 潤一郎
    • Organizer
      中化連特別講演会「創発する有機化学」
    • Place of Presentation
      中部大学
    • Year and Date
      2014-11-30
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 芳香環直接連結法による生物活性分子の合成2014

    • Author(s)
      山口 潤一郎
    • Organizer
      第32回メディシナルケミストリーシンポジウム
    • Place of Presentation
      神戸国際会議場
    • Year and Date
      2014-11-27
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 実践的合成研究を指向したC–Hカップリング反応の開発2014

    • Author(s)
      山口 潤一郎
    • Organizer
      平成26年度 後期(秋季)有機合成化学講習会
    • Place of Presentation
      日本薬学会長井記念館長井記念ホール
    • Year and Date
      2014-11-21
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 芳香環直接連結反応の開発とその展開2014

    • Author(s)
      山口 潤一郎
    • Organizer
      興和特別講演会
    • Place of Presentation
      興和東京創薬研究所
    • Year and Date
      2014-07-02
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 分子を自在に繋げるためのトライアルアンドエラー2014

    • Author(s)
      山口 潤一郎
    • Organizer
      第二回慶應有機化学若手シンポジウム
    • Place of Presentation
      慶應大学
    • Year and Date
      2014-05-10
    • Related Report
      2014 Annual Research Report
    • Invited
  • [Presentation] 標的指向型芳香環直接連結法の開発とその展開

    • Author(s)
      山口潤一郎
    • Organizer
      万有札幌シンポジウム
    • Place of Presentation
      札幌
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Synthesis of bio-molecules via direct multi-bond functionalization

    • Author(s)
      山口潤一郎
    • Organizer
      微生物化学研究所講演会
    • Place of Presentation
      微生物化学研究所
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 分子直接連結反応の開発と生物活性分子の合成

    • Author(s)
      山口潤一郎
    • Organizer
      東京大学化学生命工学専攻 2013年度 第2回談話会
    • Place of Presentation
      東京大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Book] Transition Metal-Catalyzed Heterocycle Synthesis via C-H Activation2016

    • Author(s)
      山口潤一郎、天池一真、伊丹健一郎
    • Total Pages
      45
    • Publisher
      Wiley-VCH
    • Related Report
      2015 Annual Research Report
  • [Book] Metal-catalyzed cross-coupling reactions and more2014

    • Author(s)
      山口潤一郎、伊丹健一郎
    • Total Pages
      72
    • Publisher
      Wiley
    • Related Report
      2013 Annual Research Report
  • [Remarks] 触媒で体内時計のリズムを変える ~ ほ乳類の概日リズムの周期を変える新しい分子の発見 ~

    • URL

      http://www.itbm.nagoya-u.ac.jp/ja/research/2015/06/Itami-Yoshimura-Irle-Clock.php

    • Related Report
      2015 Annual Research Report
  • [Remarks] エステル化合物と有機ホウ素化合物を切ってつなげる新反応

    • URL

      http://www.itbm.nagoya-u.ac.jp/ja/research/2015/06/Itami-NickelSM.php

    • Related Report
      2015 Annual Research Report
  • [Remarks] 置換ベンゼンを意のままにつくる ~世界初、完全非対称6置換アリールベンゼンの合成と単離~

    • URL

      http://www.itbm.nagoya-u.ac.jp/ja/research/2015/01/Itami-HAB.php

    • Related Report
      2014 Annual Research Report
  • [Remarks] 触媒反応の「合わせ技」で海洋天然物を短工程で合成

    • URL

      http://www.itbm.nagoya-u.ac.jp/ja/research/2015/01/Itami-Dictyodendrins.php

    • Related Report
      2014 Annual Research Report
  • [Remarks] ベンゾオキサゾールとフェノール誘導体のカップリング ~塩基の役割を解析~

    • URL

      http://www.itbm.nagoya-u.ac.jp/ja/research/2014/10/Nidcype-mechanism.php

    • Related Report
      2014 Annual Research Report
  • [Patent(Industrial Property Rights)] ビ(ヘテロ)アリール(チオ)エーテル化合物の製造方法2016

    • Inventor(s)
      瀧瀬瞭介、山口潤一郎、伊丹健一郎
    • Industrial Property Rights Holder
      瀧瀬瞭介、山口潤一郎、伊丹健一郎
    • Industrial Property Rights Type
      特許
    • Filing Date
      2016-03-08
    • Related Report
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] パラジウム錯体、該パラジウム錯体を用いたカップリング反応、及び該カップリング反応を用いた有機アルキン化合物の製造方法2016

    • Inventor(s)
      瀧瀬瞭介、熊澤一将、山口潤一郎、伊丹健一郎
    • Industrial Property Rights Holder
      瀧瀬瞭介、熊澤一将、山口潤一郎、伊丹健一郎
    • Industrial Property Rights Type
      特許
    • Filing Date
      2016-03-08
    • Related Report
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] γターン構造を有する化合物及びそれを用いたLSD1阻害剤2016

    • Inventor(s)
      伊丹健一郎、山口潤一郎、荒木未紗保、鈴木孝禎など
    • Industrial Property Rights Holder
      伊丹健一郎、山口潤一郎、荒木未紗保、鈴木孝禎など
    • Industrial Property Rights Type
      特許
    • Filing Date
      2016-03-29
    • Related Report
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] 多置換芳香族化合物及びその製造方法2015

    • Inventor(s)
      鈴木真、伊丹健一郎、山口潤一郎
    • Industrial Property Rights Holder
      鈴木真、伊丹健一郎、山口潤一郎
    • Industrial Property Rights Type
      特許
    • Filing Date
      2015-05-15
    • Related Report
      2015 Annual Research Report
  • [Patent(Industrial Property Rights)] 配位子、該配位子を含むニッケル錯体、及び該ニッケル錯体を用いた反応2014

    • Inventor(s)
      伊丹健一郎、山口潤一郎、瀧瀬瞭介
    • Industrial Property Rights Holder
      伊丹健一郎、山口潤一郎、瀧瀬瞭介
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2014-048094
    • Filing Date
      2014-03-11
    • Related Report
      2013 Annual Research Report

URL: 

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

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