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Development of catalytic transformations that include multiple bond cleavages and formations

Research Project

Project/Area Number 25410054
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionTokyo University of Science

Principal Investigator

Matsuda Takanori  東京理科大学, 理学部, 准教授 (80359778)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2014: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsロジウム / パラジウム / 金 / 環化 / 炭素-炭素結合切断 / 複素環式化合物 / 多置換ベンゼン / 触媒 / 酸化 / 結合切断 / 結合生成 / 芳香族化合物 / 有機合成 / メタセシス / 合成 / シクロプロペノン / 金触媒 / スピロ環化 / 炭素ー炭素結合切断 / ヒドラジン / ロジウム触媒 / インドール / 炭素-水素結合活性化
Outline of Final Research Achievements

In this study, research on catalytic transformations involving multiple bond cleavages and formations was conducted, and more than ten reactions were developed. Spirobiindanones, arylideneindanes, and dihydrophenanthrenes were synthesized by rhodium-catalyzed arylation. Ring-opening coupling reactions of cyclopropenones afforded alkenyl alkynyl ketones and spirocyclic cyclopentanones. Hydrazine derivatives underwent rhodium-catalyzed cyclization reactions to give indoles and phthalazinones. Maleic anhydrides coupled with alkynes and diynes to afford pyrones and benzenes, respectively. Rhodium-catalyzed reaction of pyridylmethylenecyclobutanes gave indanes through a skeletal rearrangement. On the other hand, pyridylmethylenecyclobutenes underwent rhodium-catalyzed intermolecular coupling with alkynes to afford multisubstituted benzenes.

Report

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

    (42 results)

All 2016 2015 2014 2013 Other

All Journal Article (13 results) (of which Peer Reviewed: 13 results,  Acknowledgement Compliant: 7 results) Presentation (26 results) (of which Int'l Joint Research: 1 results) Book (3 results)

  • [Journal Article] Ruthenium-Catalyzed Cycloisomerization of 2,2′-Diethynyl- biphenyls Involving Cleavage of a Carbon–Carbon Triple Bond2016

    • Author(s)
      Takanori Matsuda, Kotaro Kato, Tsuyoshi Goya, Shingo Shimada, and Masahiro Murakami
    • Journal Title

      Chemistry - A European Journal

      Volume: 22 Issue: 6 Pages: 1941-1943

    • DOI

      10.1002/chem.201504937

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium(III)-Catalyzed [2+2+2] Cyclotrimerization of Diynes with Maleic Anhydrides as Alkyne Equivalents2015

    • Author(s)
      Takanori Matsuda and Kentaro Suzuki
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2015 Issue: 14 Pages: 3032-3035

    • DOI

      10.1002/ejoc.201500252

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium-Catalyzed Addition/Spirocyclization of Arylboronic Esters Containing β-Aryl α,β-Unsaturated Ester Moiety2015

    • Author(s)
      Takanori Matsuda, Satoshi Yasuoka, Shoichi Watanuki, and Keisuke Fukuhara
    • Journal Title

      Synlett

      Volume: 26 Issue: 09 Pages: 1233-1237

    • DOI

      10.1055/s-0034-1378691

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Oxidative Cyclization of Dialdehydes with Alcohols and 1,3-Dicarbonyl Compounds under Rh(III)/Cu(II) Conditions2015

    • Author(s)
      Takanori Matsuda, Kentaro Suzuki, Shinya Abe, Haruki Kirikae, and Noboru Okada
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 49 Pages: 9264-9270

    • DOI

      10.1016/j.tet.2015.10.034

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium-catalysed arylative annulation of 1,4-enynes with arylboronic acids2015

    • Author(s)
      Takanori Matsuda and Shoichi Watanuki
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 13 Issue: 3 Pages: 702-705

    • DOI

      10.1039/c4ob02210f

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Synthesis of 2-acyl-1-naphthols by gold-catalyzed oxidative cyclization of 2-alkenylphenyl alkynyl ketones2015

    • Author(s)
      Takanori Matsuda, Yahiro Nishida, Kentaro Yamanaka, and Yusuke Sakurai
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 5 Pages: 869-874

    • DOI

      10.1016/j.tet.2014.12.041

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] A rhodium(I)-catalysed formal intramolecular C-C/C-H bond metathesis2015

    • Author(s)
      Takanori Matsuda and Itaru Yuihara
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 34 Pages: 7393-7396

    • DOI

      10.1039/c5cc01415h

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium(III)-catalysed decarbonylative coupling of maleic anhydrides with alkynes2014

    • Author(s)
      Takanori Matsuda and Kentaro Suzuki
    • Journal Title

      RSC Advances

      Volume: 4 Issue: 70 Pages: 37138-37141

    • DOI

      10.1039/c4ra06452f

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Rhodium-catalyzed arylation of acylsilanes with sodium tetraarylborates2014

    • Author(s)
      Takanori Matsuda, Kohei Mizuno, and Shoichi Watanuki
    • Journal Title

      Journal of Organometallic Chemistry

      Volume: 765 Pages: 64-67

    • DOI

      10.1016/j.jorganchem.2014.05.005

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Gold(I)-Catalyzed Ring-Expanding Spiroannulation of Cyclopropenones with Enynes2014

    • Author(s)
      Takanori Matsuda and Yusuke Sakurai
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 79 Issue: 6 Pages: 2739-2745

    • DOI

      10.1021/jo500045n

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rhodium(III)-Catalyzed Synthesis of Indoles from 1-Alkylidene-2-arylhydrazines and Alkynes via C-H and N-N Bond Cleavages2014

    • Author(s)
      Takanori Matsuda and Yuki Tomaru
    • Journal Title

      Tetrahedron Letters

      Volume: 印刷中 Issue: 22 Pages: 3302-3304

    • DOI

      10.1016/j.tetlet.2014.04.016

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Ring-Opening Alkynylation of Cyclopropenones2013

    • Author(s)
      Takanori Matsuda and Yusuke Sakurai
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 2013 Issue: 20 Pages: 4219-4222

    • DOI

      10.1002/ejoc.201300220

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Rhodium-Catalyzed Cross-Coupling of Alkenyl Halides with Arylboron Compounds2013

    • Author(s)
      Takanori Matsuda, Kentaro Suzuki, and Norio Miura
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 355 Issue: 17 Pages: 3396-3400

    • DOI

      10.1002/adsc.201300482

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] Rhodium(III)-Catalyzed Coupling Reactions of Carboxylic Anhydrides2015

    • Author(s)
      Takanori Matsuda and Kentaro Suzuki
    • Organizer
      16th Tetrahedron Symposium Asia Edition
    • Place of Presentation
      上海(中華人民共和国)
    • Year and Date
      2015-11-11
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ロジウム(III)触媒によるベンズアミドとシクロプロペノンの[4+3]型環化反応2015

    • Author(s)
      山中健太郎、松田学則
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀(東京都、江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] シクロブテンとアルキンのロジウム触媒分子間カップリングによる多置換ベンゼンの合成2015

    • Author(s)
      松本剛史、松田学則
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀(東京都、江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] ロジウム触媒によるベンゾシクロ[3.3]ヘプタン誘導体の連続的炭素-炭素結合切断を経由する骨格再構築反応2015

    • Author(s)
      油井原格、松田学則
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      タワーホール船堀(東京都、江戸川区)
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] 炭素―炭素結合および炭素―水素結合の切断を経由するフェニルシクロブタンのインダンへのロジウム触媒転位反応2015

    • Author(s)
      油井原格、松田学則
    • Organizer
      第62回有機金属化学討論会
    • Place of Presentation
      関西大学千里山キャンパス(大阪府、吹田市)
    • Year and Date
      2015-09-09
    • Related Report
      2015 Annual Research Report
  • [Presentation] Formation of Indane Frameworks via 1,4-Rhodium Migration2014

    • Author(s)
      Takanori Matsuda, Satoshi Yasuoka, Shoichi Watanuki, and Itaru Yuihara
    • Organizer
      8th Singapore International Chemistry Conference
    • Place of Presentation
      Singapore, Singapore
    • Year and Date
      2014-12-16
    • Related Report
      2014 Research-status Report
  • [Presentation] Transition-Metal-Catalysed Annulation Reactions of Cyclopropenones2014

    • Author(s)
      Takanori Matsuda and Yusuke Sakurai
    • Organizer
      18th Malaysian International Chemical Congress
    • Place of Presentation
      Kuala Lumpur, Malaysia
    • Year and Date
      2014-11-05
    • Related Report
      2014 Research-status Report
  • [Presentation] Rhodium(I)-Catalyzed Ring Opening Reactions of Methylenecyclobutanes2014

    • Author(s)
      Takanori Matsuda, Yuya Suda, Itaru Yuihara, and Akira Takahashi
    • Organizer
      Conference on C-C Bond Cleavage
    • Place of Presentation
      Kyoto, Japan
    • Year and Date
      2014-10-25
    • Related Report
      2014 Research-status Report
  • [Presentation] ロジウム触媒による1-アリール-3-(2-ピリジルメチレン)シクロブタンの骨格再構築反応2014

    • Author(s)
      油井原格、松田学則
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2014-10-16
    • Related Report
      2014 Research-status Report
  • [Presentation] 金触媒を用いた酸化的環化反応による2-アシル-1-ナフトール誘導体の合成2014

    • Author(s)
      山中健太郎、西田八尋、櫻井雄介、松田学則
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2014-10-15
    • Related Report
      2014 Research-status Report
  • [Presentation] ロジウム(Ⅲ)触媒による無水マレイン酸とアルキンの酸化的環化反応2014

    • Author(s)
      鈴木健太郎、松田学則
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2014-10-15
    • Related Report
      2014 Research-status Report
  • [Presentation] 1,4-ロジウム移動を経由する1,4-エンインのアリール化/環化反応2014

    • Author(s)
      綿貫勝一、松田学則
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2014-10-15
    • Related Report
      2014 Research-status Report
  • [Presentation] ロジウム触媒分子内C≡C/C=N結合メタセシスによるフタラジノン骨格形成2014

    • Author(s)
      松田祥弥、松田学則
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2014-10-15
    • Related Report
      2014 Research-status Report
  • [Presentation] Transition-Metal-Catalyzed Annulation Reactions of Cyclopropenones2014

    • Author(s)
      Takanori Matsuda and Yusuke Sakurai
    • Organizer
      5th EuCheMS Chemistry Congress
    • Place of Presentation
      Istanbul, Turkey
    • Year and Date
      2014-09-03
    • Related Report
      2014 Research-status Report
  • [Presentation] ロジウム触媒による1-アリール-3-(2-ピリジルメチレン)シクロブタンの骨格再構築反応

    • Author(s)
      松田学則、油井原格
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] 無水マレイン酸をアルキン等価体として用いるロジウム(III)触媒[2 + 2 + 2]環化付加反応

    • Author(s)
      鈴木健太郎、松田学則
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] 金触媒によるエンインとシクロプロペノンのスピロ環化反応

    • Author(s)
      櫻井雄介、松田学則
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、東山キャンパス
    • Related Report
      2013 Research-status Report
  • [Presentation] 1,5-ロジウム移動を経由するo-アルキニルビフェニルのアリール化/環化反応

    • Author(s)
      綿貫勝一、松田学則
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2013 Research-status Report
  • [Presentation] パラジウム触媒によるフタラジノン骨格形成反応の開発

    • Author(s)
      松田祥弥、戸丸祐岐、松田学則
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2013 Research-status Report
  • [Presentation] ロジウム触媒によるハロゲン化アルケニルのアリール化反応

    • Author(s)
      鈴木健太郎、三浦律男、松田学則
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2013 Research-status Report
  • [Presentation] ロジウム触媒によるシクロプロペノンと1,6-エンインの[2 + 2 + 2]環化付加反応

    • Author(s)
      櫻井雄介、松田学則
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2013 Research-status Report
  • [Presentation] ロジウム触媒による無水マレイン酸とアルキンの形式的[5-1+2]環化反応

    • Author(s)
      鈴木健太郎、松田学則
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 金触媒によるエンインとシクロプロペノンのスピロ環化反応

    • Author(s)
      櫻井雄介、松田学則
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] Rhodium(I)-Catalyzed Ring-Opening Benzannulation of Cyclobutenols with Alkynes

    • Author(s)
      Takanori Matsuda and Norio Miura
    • Organizer
      The 2nd International Conference of the Indonesian Chemical Society (ICICS-2013)
    • Place of Presentation
      Yogyakarta, Indonesia
    • Related Report
      2013 Research-status Report
  • [Presentation] Catalytic Construction of Spiro[4.4]nonane Skeletons through Cleavage of Unreactive Bonds

    • Author(s)
      Takanori Matsuda, Yuya Suda, Satoshi Yasuoka, and Yusuke Sakurai
    • Organizer
      15th Asian Chemical Congress (15ACC)
    • Place of Presentation
      Singapore
    • Related Report
      2013 Research-status Report
  • [Presentation] Rhodium-Catalyzed Synthesis of Silole Derivatives

    • Author(s)
      Takanori Matsuda, Yosuke Fujisaki, Yoichiro Ichioka, and Yuya Suda
    • Organizer
      24th International Society of Heterocyclic Chemistry Congress (ISHC-24)
    • Place of Presentation
      Shanghai, China
    • Related Report
      2013 Research-status Report
  • [Book] Cleavage of Carbon-Carbon Single Bonds by Transition Metals2015

    • Author(s)
      Takanori Matsuda
    • Total Pages
      278
    • Publisher
      Wiley-VCH
    • Related Report
      2015 Annual Research Report
  • [Book] Comprehensive Organic Synthesis II, Volume 52014

    • Author(s)
      Masahiro Murakami and Takanori Matsuda
    • Total Pages
      51
    • Publisher
      Elsevier Ltd.
    • Related Report
      2013 Research-status Report
  • [Book] Transition-Metal-Mediated Aromatic Ring Construction2013

    • Author(s)
      Takanori Matsuda
    • Total Pages
      11
    • Publisher
      John Wiley & Sons, Inc.
    • Related Report
      2013 Research-status Report

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

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