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Activation of chemical bonds between main-elements in body by multifunctional copper catalysts

Research Project

Project/Area Number 23685008
Research Category

Grant-in-Aid for Young Scientists (A)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionTohoku University

Principal Investigator

NAKAMURA Itaru  東北大学, 理学(系)研究科(研究院), 准教授 (00333899)

Project Period (FY) 2011-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥28,990,000 (Direct Cost: ¥22,300,000、Indirect Cost: ¥6,690,000)
Fiscal Year 2013: ¥9,360,000 (Direct Cost: ¥7,200,000、Indirect Cost: ¥2,160,000)
Fiscal Year 2012: ¥9,360,000 (Direct Cost: ¥7,200,000、Indirect Cost: ¥2,160,000)
Fiscal Year 2011: ¥10,270,000 (Direct Cost: ¥7,900,000、Indirect Cost: ¥2,370,000)
Keywords結合活性化 / 銅触媒 / ヘテロ環 / 転位反応 / ドミノ反応 / 効率的合成 / 環境調和型分子変換 / 触媒反応 / 骨格転位 / 結合切断 / ロジウム触媒 / 水溶性配位子 / 不斉転写
Outline of Final Research Achievements

In this investigation, we developed several synthetic reactions involving cleavage of sigma bonds between "main elements in body" by the use of multi-functional copper catalysts. In particular, we developed skeletal rearrangement and cascade reactions employing O-propargylic oximes as the substrate. These reaction involves cleavage of C-O and/or N-O bonds. Copper catalysts consecutively functioned not only pi-activation catalyst but also sigma acids and single-electron transfer catalysts. Moveover, our investigations realized efficient synthesis of new class of heterocyclic compounds, such as four-membered cyclic nitrones, pyridine-N-oxides, dihydropyrimidines, triazines, and oxazepines.

Report

(4 results)
  • 2014 Final Research Report ( PDF )
  • 2013 Annual Research Report
  • 2012 Annual Research Report
  • 2011 Annual Research Report
  • Research Products

    (31 results)

All 2015 2014 2013 2012 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results,  Open Access: 2 results) Presentation (19 results) (of which Invited: 9 results) Remarks (2 results)

  • [Journal Article] Cu-Catalyzed Skeletal Rearrangement of O-Propargylic Electron-Rich-Arylaldoximes into Amidodienes2014

    • Author(s)
      Nakamura, I.; Ishida, Y.; Terada, M.
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 9 Pages: 2562-2565

    • DOI

      10.1021/ol5009608

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Synthesis of Eight-Membered Nitrogen-Heterocycles from O-Propargylic Oximes via Rh-Catalyzed Cascade Reactions2014

    • Author(s)
      Nakamura, I.; Sato, Y.; Takeda, K.; Terada, M.
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 33 Pages: 10214-10219

    • DOI

      10.1002/chem.201403637

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] N-Allenylnitrone Acts as 2-Azadiene in the Cu-Catalyzed Cascade Reaction of O-Propargylic Oximes with Azodicarboxylates2014

    • Author(s)
      中村 達、城 健、張 冬、寺田 眞浩
    • Journal Title

      Organic Chemistry Frontiers

      Volume: 1 Issue: 8 Pages: 914-918

    • DOI

      10.1039/c4qo00156g

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Efficient Synthesis of N-Alkylated alpha,beta-Unsaturated Ketonitrones via Cu-Catalyzed Rearrangement2014

    • Author(s)
      Nakamura, I.; Onuma, T.; Kanazawa, R.; Nishigai, Y.; Terada, M.
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 16 Pages: 4198-4200

    • DOI

      10.1021/ol501889g

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Cascade Transformation of O-Propargylic Oximes with Sulfonyl Azides to α,β-Unsaturated N-Acylamidines2014

    • Author(s)
      張 冬、中村 達、寺田 眞浩
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 19 Pages: 5184-5187

    • DOI

      10.1021/ol502541w

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Heterocyclic Synthesis by pi-Acidic Metal Catalyzed Reactions via N-O Bond Cleavage2014

    • Author(s)
      Nakamura, I.; Terada, M.
    • Journal Title

      Heterocycles

      Volume: 89 Issue: 4 Pages: 845-868

    • DOI

      10.3987/rev-13-791

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Cu-Catalyzed Skeletal Rearrangement of O-Propargylic Aryloximes into Four-Membered Cyclic Nitrones - Chirality Transfer and Mechanistic Insight2012

    • Author(s)
      Itaru Nakamura, Yu Kudo, Toshiharu Araki, Dong Zhang, Eunsang Kwon, Masahiro Terada
    • Journal Title

      Synthesis

      Volume: 44 Issue: 10 Pages: 1542-1550

    • DOI

      10.1055/s-0031-1290819

    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of Azepine Derivatives via Rh-Catalyzed Tandem 2,3- Rearrangement - Heterocyclization2012

    • Author(s)
      Itaru Nakamura, Masashi Okamoto, Yoshinori Sato, Masahiro Terada
    • Journal Title

      Angewandte Chemie, International Edition

      Volume: 51 Issue: 43 Pages: 10816-10819

    • DOI

      10.1002/anie.201205285

    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 多置換ヘテロ環の構築を志向するπ酸性遷移金属触媒反応の開発2012

    • Author(s)
      中村達
    • Journal Title

      有機合成化学協会誌

      Volume: 70 Pages: 581-592

    • NAID

      10030765740

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 多置換ヘテロ感の構築を志向するπ酸性遷移金属触媒反応の開発2012

    • Author(s)
      中村達
    • Journal Title

      有機合成化学協会誌

      Volume: 70 Pages: 581-592

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] Catalytic Transformations of O-Propargylic Oximes2015

    • Author(s)
      Itaru Nakamura
    • Organizer
      Asian International Symposium; Organic Chemistry / Green Sustainable Chemistry, 95th annual meeting, CSJ
    • Place of Presentation
      船橋
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Catalytic Skeletal Rearrangement of O-Propargylic Oximes via C=N Bond Cleavage2014

    • Author(s)
      Itaru Nakamura
    • Organizer
      5th Symposium for Young Chemists on Molecular Activation
    • Place of Presentation
      阿蘇
    • Year and Date
      2014-12-19 – 2014-12-20
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Catalytic Transformations of O-Propargylic Oximes2014

    • Author(s)
      Itaru Nakamura
    • Organizer
      the 8th Singapore International Chemistry Conference (SICC-8)
    • Place of Presentation
      シンガポール、シンガポール
    • Year and Date
      2014-12-14 – 2014-12-17
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Cu-Catalyzed Skeletal Rearrangement of O-Propargylic Electron-Rich Arylaldoximes to Amidodienes2014

    • Author(s)
      Itaru Nakamura, Yasuhiro Ishida, Masahiro Terada
    • Organizer
      The 2nd International Conference on Organometallics and Catalysis (OM&Cat2014)
    • Place of Presentation
      奈良
    • Year and Date
      2014-10-26 – 2014-10-29
    • Related Report
      2013 Annual Research Report
  • [Presentation] C=N結合の開裂を伴うプロパルギルオキシムの骨格転位反応2014

    • Author(s)
      中村 達
    • Organizer
      2014複素環化学研究会
    • Place of Presentation
      札幌
    • Year and Date
      2014-09-12 – 2014-09-13
    • Related Report
      2013 Annual Research Report
  • [Presentation] O-プロパルギルオキシムとイソシアネートとのカスケード反応によるジヒドロピリミジンの合成2014

    • Author(s)
      中村 達・小沼俊輝・張 冬・寺田眞浩
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌
    • Year and Date
      2014-09-10 – 2014-09-12
    • Related Report
      2013 Annual Research Report
  • [Presentation] 触媒的骨格転位反応を鍵とする新規ヘテロ環構築手法の開発2014

    • Author(s)
      中村 達
    • Organizer
      東京理科大学総合化学研究科
    • Place of Presentation
      東京
    • Year and Date
      2014-07-23
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Cu-Catalyzed Skeletal Rearrangement of O-Propargylic Electron-Rich Arylaldoximes to Amidodienes2014

    • Author(s)
      Itaru Nakamura
    • Organizer
      the XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-13 – 2014-07-18
    • Related Report
      2013 Annual Research Report
  • [Presentation] Efficient Synthesis of Medium-Sized Nitrogen Heterocycles from O-Propargylic Oximes via Rh-Catalyzed Cascade Reaction2014

    • Author(s)
      Itaru Nakamura, Masashi Okamoto, Yoshinori Sato, Keisuke Takeda, and Masahiro Terada
    • Organizer
      the 19th International Symposium on Homogeneous Catalysis (ISHC-XIX)
    • Place of Presentation
      オタワ、カナダ
    • Year and Date
      2014-07-06 – 2014-07-11
    • Related Report
      2013 Annual Research Report
  • [Presentation] O-プロパルギルオキシムの触媒的骨格転位反応2014

    • Author(s)
      中村 達
    • Organizer
      第49回天然物化学談話会
    • Place of Presentation
      岡山
    • Year and Date
      2014-07-02 – 2014-07-04
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 触媒的骨格転位を鍵とする新しいヘテロ環構築反応2014

    • Author(s)
      中村 達
    • Organizer
      有機合成化学協会九州山口支部有機合成化学講演会-合成有機化学のフロンティア-
    • Place of Presentation
      福岡
    • Year and Date
      2014-06-06
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] O-プロパルギルオキシムの触媒的骨格転位反応2014

    • Author(s)
      中村 達
    • Organizer
      慶応義塾大学理工学部応用化学科
    • Place of Presentation
      横浜
    • Year and Date
      2014-05-30
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] Catalytic Skeletal Rearrangement of O-Propargylic Oximes2013

    • Author(s)
      Itaru Nakamura
    • Organizer
      Asian International Symposium-Organic Chemistry /Green Sustainable Chemistry, 93th annual meeting, CSJ
    • Place of Presentation
      草津
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] Catalytic Skeletal Rearrangement of O-Propargylic Oxime2013

    • Author(s)
      Itaru Nakamura
    • Organizer
      Asian International Symposium-Organic Chemistry /Green Sustainable Chemistry, 93th annual meeting, CSJ
    • Place of Presentation
      草津
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] Cu-catalyzed skeletal rearrangement of O-propargylic oximes via C-O and N-O bond cleavage2012

    • Author(s)
      Itaru NAKAMURA, Yu KUDO, Tomoki IWATA, Toshiharu ARAKI, Dong ZHANG, Eunsang KWON, and Masahiro TERADA
    • Organizer
      18th International Symposium on Homogeneous Catalysis (ISHC-18)
    • Place of Presentation
      トゥールーズ、フランス
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
  • [Presentation] Cu-Catalyzed Skeletal Rearrangement of O-Propargylic Oximes2012

    • Author(s)
      Itaru Nakamura, Yu Kudo, Tomoki Iwata, Toshiharu Araki, Dong Zhang, Eunsang Kwon, Masahiro Terada
    • Organizer
      25th International Conference on Organometallic Chemistry (ICOMC-25)
    • Place of Presentation
      リスボン、ポルトガル
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
  • [Presentation] ロジウム触媒を用いたタンデム型[2,3]転位-ヘテロ環化反応によるアゼピン誘導体の合成2012

    • Author(s)
      中村 達、岡本真士、佐藤良紀、寺田眞浩
    • Organizer
      第42回複素環化学討論会
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
  • [Presentation] Rearrangement-Cycloaddition-Rearrangement Cascade in Cu-Catalyzed Reaction2012

    • Author(s)
      Itaru Nakamura
    • Organizer
      2nd International Symposium on Molecular Activation
    • Place of Presentation
      奈良
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
  • [Presentation] Synthesis of Azepine Derivatives via Rh-Catalyzed Tandem 2,3- Rearrangement-Heterocyclization2012

    • Author(s)
      Itaru Nakamura, Masashi Okamoto, Yoshinori Sato, Masahiro Terada
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry (IKCOC-12)
    • Place of Presentation
      京都
    • Related Report
      2012 Annual Research Report 2011 Annual Research Report
  • [Remarks] 東北大学大学院理学研究科化学専攻反応有機化学研究室

    • URL

      http://www.orgreact.sakura.ne.jp/index.html

    • Related Report
      2013 Annual Research Report
  • [Remarks] 東北大学大学院理学研究科化学専攻反応有機化学研究室

    • URL

      http://www.orgreact.sakura.ne.jp/

    • Related Report
      2012 Annual Research Report

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Published: 2011-04-06   Modified: 2019-07-29  

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