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Development of new synthetic methodologies based on photochemical carbene formation reaction

Research Project

Project/Area Number 23350016
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionGakushuin University (2013)
Tokyo Institute of Technology (2011-2012)

Principal Investigator

KUSAMA Hiroyuki  学習院大学, 理学部, 教授 (30242100)

Project Period (FY) 2011-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥10,920,000 (Direct Cost: ¥8,400,000、Indirect Cost: ¥2,520,000)
Fiscal Year 2013: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Fiscal Year 2012: ¥5,460,000 (Direct Cost: ¥4,200,000、Indirect Cost: ¥1,260,000)
Keywordsカルベン / 光反応 / 炭素骨格形成反応 / アシルシラン / 光異性化 / カップリング / 有機ホウ素化合物 / クロスカップリング / イリド / 付加環化 / ボロン酸
Outline of Final Research Achievements

We have investigated the development of new and clean synthetic methodologies by using photochemical processes without aid of metal catalysts.
Photochemical generation of carbenes, highly reactive intermediates, from acylsilanes has scarcely been employed for organic synthesis, so far. In this project, we examined application of this photochemical process to organic reactions with appropriate design of reaction systems and succeeded in developing several useful and original synthetic reactions.

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 2011 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (24 results) (of which Invited: 3 results)

  • [Journal Article] Chromium(0)-Catalyzed Tandem Cyclization of α,β-Unsaturated Thioimi dates Containing an Enyne Moiety2012

    • Author(s)
      Y.Karibe, H.Kusama, N.Iwasawa
    • Journal Title

      Angewandte Chemie International Edition

      Volume: (掲載確定) Issue: 25 Pages: 6214-6218

    • DOI

      10.1002/anie.201201505

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Selective Intermolecular [2+2] Cycloaddition Reaction Using Platinum(II) Catalyst with Hollow-shaped Triethynyl Phosphine2012

    • Author(s)
      Masaru Ebisawa
    • Journal Title

      Chemistry Letters

      Volume: 41 Issue: 8 Pages: 786-788

    • DOI

      10.1246/cl.2012.786

    • NAID

      130004426638

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Platinum(II)-Catalyzed Generation and [3+2] Cycloaddition Reaction of α,β-Unsaturated Carbene Complex Intermediates for the Preparation of Polycylic Compounds2011

    • Author(s)
      Kodai Saito
    • Journal Title

      Journal of the American Chemical Sosiety

      Volume: 133 Issue: 4 Pages: 689-691

    • DOI

      10.1021/ja108586d

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Rhenium(I)- and Tungsten(0)-Catalyzed Tandem Cyclization of Acetylenic Dienol Silyl Ethers Based on Geminal Carbo-Functionalization of Alkynes2011

    • Author(s)
      H.Kusama, Y.Karibe, R.Imai, Y.Onizawa, H.Yamabe, N.Iwasawa
    • Journal Title

      Chemistry-A European Journal

      Volume: 17 Issue: 17 Pages: 4839-4848

    • DOI

      10.1002/chem.201003019

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photochemically Promoted Transition Metal-Free Cross-Coupling of Acylsilanes with Organoboronic Esters2011

    • Author(s)
      K.Ito, H.Tamashima, N.Iwasawa, H.Kusama
    • Journal Title

      J.Am.Chem.Soc.

      Volume: 133 Issue: 11 Pages: 3716-3719

    • DOI

      10.1021/ja1102597

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] [3+2]Cycloaddition of Metal-Containing Azomethine Ylides for Highly Efficient Synthesis of Mitosene Skeleton2011

    • Author(s)
      J.Takaya, Y.Miyashita, H.Kusama, N.Iwasawa
    • Journal Title

      Tetrahedron

      Volume: 67 Issue: 24 Pages: 4455-4466

    • DOI

      10.1016/j.tet.2011.04.017

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Efficient Ligand Control for the Cationic Platinum(II)-Catalyzed Concise Synthesis of Two Types of Fused Carbocycles with Angular Oxygen Functionality2011

    • Author(s)
      H.Kusama, E.Watanabe, K.Ishida, N.Iwasawa
    • Journal Title

      Chem.Asian J.

      Volume: 6 Issue: 9 Pages: 2273-2277

    • DOI

      10.1002/asia.201100460

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] アシルシランからのカルベン生成を活用する新規分子変換手法2015

    • Author(s)
      草間博之
    • Organizer
      第69回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      横浜
    • Year and Date
      2015-05-16
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] 光化学的に発生させたシロキシカルベン種の形式的分子内CH挿入による環状骨格構築法2015

    • Author(s)
      仲田拓馬、石井秀一、大山智也、伊藤和太、石田健人、岩澤伸治、草間博之
    • Organizer
      第95日本化学会春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-28
    • Related Report
      2013 Annual Research Report
  • [Presentation] Kinetic studies on generation and cycloaddition reaction of ylide intermediates derived from siloxycarbenes and quinolones2015

    • Author(s)
      ISHIDA, Kento; SATO, Junpei; ICHIKAWA, Kenichi; MIZUNO, Takemi; IWASAWA, Nobuharu; ABE, Manabu; KUSAMA, Hiroyuki
    • Organizer
      第95日本化学会春季年会
    • Place of Presentation
      千葉
    • Year and Date
      2015-03-27
    • Related Report
      2013 Annual Research Report
  • [Presentation] 光化学的に発生させたシロキシカルベン種の分子内C-H挿入によるジヒドロベンゾフラン類の立体選択的合成2014

    • Author(s)
      仲田拓馬、大山智也、勝本裕也、伊藤和太、石田健人、岩澤伸治、草間博之
    • Organizer
      第68回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟
    • Year and Date
      2014-11-29
    • Related Report
      2013 Annual Research Report
  • [Presentation] アシルシランの光異性化により生成するシロキシカルベンのジボロンへの形式的挿入反応2014

    • Author(s)
      芦田諒、岩澤伸治、草間博之
    • Organizer
      第94日本化学会春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      2014-03-27
    • Related Report
      2013 Annual Research Report
  • [Presentation] シロキシカルベンとピリジン類とのイリド形成とその付加環化反応2014

    • Author(s)
      市川健一、只見聡、岩澤伸治、草間博之
    • Organizer
      第94日本化学会春季年会
    • Place of Presentation
      名古屋
    • Year and Date
      2014-03-27
    • Related Report
      2013 Annual Research Report
  • [Presentation] Photo-Induced Three-Component Coupling Reaction Utilizing Electrophilic Charactor of Siloxycarbenes2013

    • Author(s)
      Kenichi Ichikawa, Satoshi Tadami, Hideyuki Sogo, Nobuharu Iwasawa, Hiroyuki Kusama
    • Organizer
      The Eighth International Symposium on Integrated Synthesis
    • Place of Presentation
      奈良
    • Year and Date
      2013-11-29
    • Related Report
      2013 Annual Research Report
  • [Presentation] Tandem Carbon-Carbon Bond Formation Utilizing Photo-Induced Coupling Reaction Between Acylsilanes and Organoboron Compounds2013

    • Author(s)
      Ryo Ashida, Tamashima Hiroto, Sasano Kota, Iwasawa Nobuharu, Kusama Hiroyuki
    • Organizer
      The Eighth International Symposium on Integrated Synthesis
    • Place of Presentation
      奈良
    • Year and Date
      2013-11-29
    • Related Report
      2013 Annual Research Report
  • [Presentation] 白金(II)触媒を用いた電子豊富アレンと電子豊富ジエンとの分子間[4+2]及び[4+3]付加環化反応

    • Author(s)
      岩澤伸治
    • Organizer
      第101回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学(東京都)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 白金(II)触媒による電子豊富アレンと電子豊富ジエンとの分子間[4+2]及び[4+3]付加環化反応

    • Author(s)
      岩澤伸治
    • Organizer
      第59回有機金属化学討論会
    • Place of Presentation
      大阪大学(大阪府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] 白金(II)触媒によるアルキンの求電子的活性化を契機とする不飽和カルベン錯体中間体の発生とその[4+3]付加環化反応

    • Author(s)
      岩澤伸治
    • Organizer
      第2回CSJフェスタ2012
    • Place of Presentation
      東京工業大学(東京都)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Synthetic Study of Yuremamine Based on [3+2] Cycloaddition of Platinum-Containing Azomethine Ylide

    • Author(s)
      Nobuharu Iwasawa
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Photochemically Promoted Cross-Coupling of Acylsilanes with Organoboron Compounds

    • Author(s)
      Hiroyuki Kusama
    • Organizer
      The 12th International Kyoto Conference on New Aspects of Organic Chemistry
    • Place of Presentation
      リーガロイヤルホテル京都(京都府)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Photochemically Promoted Transition Metal-Free Cross Coupling of Acylsilanes with Organoboron Compounds

    • Author(s)
      Hiroyuki Kusama
    • Organizer
      The 7th International Conference on Cutting-Edge Organic Chemistry in Asia
    • Place of Presentation
      Nanyang Technological University (Singapore)
    • Related Report
      2012 Annual Research Report
  • [Presentation] タングステン触媒による連続環化反応に基づくアゼパノ[1,2-a]インドール誘導体の効率的合成法

    • Author(s)
      岩澤伸治
    • Organizer
      第93日本化学会春季年会
    • Place of Presentation
      立命館大学(滋賀県)
    • Related Report
      2012 Annual Research Report
  • [Presentation] Transition Metal-Catalyzed Tandem Cyclization Reactions for Preparation of Polycyclic Indole Derivatives

    • Author(s)
      Hiroyuki Kusama
    • Organizer
      第93日本化学会春季年会
    • Place of Presentation
      立命館大学(滋賀県)
    • Related Report
      2012 Annual Research Report
    • Invited
  • [Presentation] 白金含有カルボニルイリドの[3+2]付加環化反応に基づく多環性骨格構築法

    • Author(s)
      岩澤伸治
    • Organizer
      第61回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      千葉
    • Related Report
      2011 Annual Research Report
  • [Presentation] 白金(II)触媒によるアルキンの求電子的活性化を基盤とした不飽和カルベン錯体中間体の[4+3]付加環化反応

    • Author(s)
      岩澤伸治
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋
    • Related Report
      2011 Annual Research Report
  • [Presentation] Cr(CO)5(L)-Catalyzed Tandem Cyclization of α,β-Unsaturated Thioimidate Derivatives Containing an Enyne Moiety

    • Author(s)
      Nobuharu Iwasawa
    • Organizer
      The Seventh International Symposium on Integrated Synthesis
    • Place of Presentation
      Maiko
    • Related Report
      2011 Annual Research Report
  • [Presentation] アルキンの求電子的活性化を基盤とする多環性骨格構築手法

    • Author(s)
      草間博之
    • Organizer
      有機合成化学を起点とするものづくり戦略ミニシンポジウム
    • Place of Presentation
      東京
    • Related Report
      2011 Annual Research Report
    • Invited
  • [Presentation] 白金(II)触媒による電子豊富アレンと電子豊富ジエンとの分子間[4+3]付加環化反応

    • Author(s)
      岩澤伸治
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] アシルシランの光異性化によるカルベン生成を利用した三成分カップリング反応

    • Author(s)
      草間博之
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] 白金含有カルボニルイリドの[3+2]付加環化反応を基盤とするエングレリンAの全合成

    • Author(s)
      岩澤伸治
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report
  • [Presentation] 白金含有アゾメチンイリドの[3+2]付加環化反応を基盤としたYuremamineの合成研究

    • Author(s)
      岩澤伸治
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      横浜
    • Related Report
      2011 Annual Research Report

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Published: 2013-05-15   Modified: 2019-07-29  

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