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2013 Fiscal Year Final Research Report

Synthesis of Chiral and Cyclic pai-Conjugated System Using Cycloaddition

Research Project

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Project/Area Number 22350046
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionWaseda University

Principal Investigator

SHIBATA Takanori  早稲田大学, 理工学術院, 教授 (80265735)

Project Period (FY) 2010-04-01 – 2014-03-31
Keywords共役系 / 不斉 / 環状化合物 / 触媒 / 機能性物質
Research Abstract

We achieved an easy-to-use protocol for the synthesis of substituted o,o,o,o-tetraphenylenes: two triynes with phenylene-bridged 1,5-diyne moiety was homo-coupled by consecutive inter- and intramolecular [2+2+2] cycloadditions, and tetraphenylenes were obtained with good to excellent enantiomeric excess. We further examined meta-phenylene tethered triynes and achieved the first construction of o,m,o,m-tetraphenylenes in cis-form. In addition to the tetraphenylenes as dimers, o,m,o,m,o,m-hexaphenylenes were also obtained as trimers. In the reaction of para-phenylene tethered triynes, o,p,o,p,o,p-hexaphenylenes were major products along with the formation of o,p,o,p,o,p,o,p-octaphenylenes as tetramers.

  • Research Products

    (44 results)

All 2014 2013 2012 2011 2010 Other

All Journal Article (14 results) (of which Peer Reviewed: 14 results) Presentation (29 results) (of which Invited: 9 results) Remarks (1 results)

  • [Journal Article] Enantioselective Synthesis of Planar-Chiral Phosphines with 1,N-Dioxa[n]paracyclophane Scaffold and Their Application as Chiral Ligands2014

    • Author(s)
      Kanda, K.; Oshima, S.; Shizuno, T.; Hamanaka, R.; Fukai, M.; Shibata, T.
    • Journal Title

      Heterocycles

      Volume: 88 Pages: 1355-1370

    • Peer Reviewed
  • [Journal Article] Ir(I)-Catalyzed Synthesis of N-Substituted Pyridones from 2-Alkoxypyridines via CO Bond Cleavage2013

    • Author(s)
      Pan, S; Ryu, N; Shibata, T.
    • Journal Title

      Org. Lett.

      Volume: 15 Pages: 1902-1905

    • Peer Reviewed
  • [Journal Article] Facile Synthesis of Cyclic Polyphenylenes by Consecutive Inter- and Intramolecular Cycloadditions of Ortho, Meta, and Para-Phenylene-Tethered Triynes2012

    • Author(s)
      Shibata, T. ; Fujimoto, M; Hirashima, H; Chiba, T; Endo, K. Synthesis
    • Journal Title

      Feature Article

      Volume: 44 Pages: 3269-3284

    • Peer Reviewed
  • [Journal Article] Reversal enantioselectivity induced by achiral alcohols in asymmetric autocatalysis in the presence of a chiral diol as a chiral initiator2012

    • Author(s)
      Shibata, T ; Tarumi, H; Kawasaki, T; Soai, K.
    • Journal Title

      Tetrahedron : Asymmetry

      Volume: 23 Pages: 1023-1027

    • Peer Reviewed
  • [Journal Article] Ir(I)-Catalyzed Intermolecular Regio- and Enantioselective Hydroamination of Alkenes with Heteroaromatic Amines2012

    • Author(s)
      Pan, S.; Endo, K.; Shibata, T.
    • Journal Title

      Org. Lett.

      Volume: 14 Pages: 780-783

    • Peer Reviewed
  • [Journal Article] Highly enantioselective synthesis of silahelicenes using Ir-catalyzed [2+2+2] cycloaddition2012

    • Author(s)
      Shibata, T. ; Uchiyama, T.; Yoshinami, Y.; Takayasu, S.; Tsuchikama, K.; Endo, K.
    • Journal Title

      Chem. Commun.

      Volume: 48 Pages: 1311-1313

    • Peer Reviewed
  • [Journal Article] Asymmetric ortho-lithiation of 1,n-dioxa[n]paracyclophane derivatives for the generation of planar chirality2012

    • Author(s)
      Kanda, K.; Hamanaka, R.; Endo, K.; Shibata, T.
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 1407-1416

    • Peer Reviewed
  • [Journal Article] Enantioselective synthesis of tripodal cyclophanes and pyridinophanes by intramolecular [2+2+2] cycloaddition2012

    • Author(s)
      Shibata, T. ; Miyoshi, M.; Uchiyama, T.; Endo, K.; Miura, N.; Monde, K.
    • Journal Title

      Tetrahedron

      Volume: 68 Pages: 2679-2686

    • Peer Reviewed
  • [Journal Article] Ru-catalyzed β-selective and enantioselective addition of amines to styrenes initiated by direct arene-exchange2012

    • Author(s)
      Otsuka, M.; Yokoyama, H.; Endo, K.; Shibata, T .
    • Journal Title

      Org. Biomol. Chem.

      Volume: 10 Pages: 3815-3818

    • Peer Reviewed
  • [Journal Article] Enantioselective construction of new chiral cyclic scaffolds using [2 + 2 + 2] cycloaddition2011

    • Author(s)
      Shibata, T. ; Uchiyama, T.; Hirashima, H.; Endo, K.
    • Journal Title

      Pure Appl. Chem.

      Volume: 83 Pages: 597-605

    • Peer Reviewed
  • [Journal Article] Facile Catalytic S_Nar Reaction of Nonactivated Fluoroarenes with Amines Using η^6 -Benzene Ru(II) Complex2010

    • Author(s)
      Otsuka, M.; Yokoyama, H.; Endo, K.; Shibata, T.
    • Journal Title

      Synlett

      Pages: 2601-2606

    • Peer Reviewed
  • [Journal Article] Enantioselective Intramolecular [2+2+2] Cycloaddition of Dienynes for the Construction of Adjacent Three Chiral Centers2010

    • Author(s)
      Shibata, T. ; Otomo, M.; Endo, K.
    • Journal Title

      Synlett

      Pages: 1235-1238

    • Peer Reviewed
  • [Journal Article] Enantioselective Synthesis of Planar-Chiral 1,n-Dioxa[n]paracyclophanes via Catalytic Asymmetric Ortho-Lithiation2010

    • Author(s)
      Kanda, K.; Endo, K.; Shibata, T.
    • Journal Title

      Org. Lett.

      Volume: 12 Pages: 1980-1983

    • Peer Reviewed
  • [Journal Article] Sequential Catalytic Reactions for the Synthesis of Benzofulvenes Using an Iridium Complex with Dual Function2010

    • Author(s)
      Tsuchikama, K.; Kasagawa, M.; Endo, K.; Shibata, T.
    • Journal Title

      Synlett

      Pages: 97-100

    • Peer Reviewed
  • [Presentation] パラシクロファン骨格を有する面不斉リン配位子のエナンチオ選択的合成と不斉カップリングへの応用2014

    • Author(s)
      大嶋 祥也, 静野 翼, 深井 実紅, 神田 和正, 柴田 高範
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋 大学(愛知)
    • Year and Date
      2014-03-29
  • [Presentation] ロジウム触媒による[2+2+2]付加環化反応を利用したジベンゾチオフェンジオキシド誘導体の効率合成2014

    • Author(s)
      峨家 愛実, 田原 優樹, 柴田 高範
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学(愛知)
    • Year and Date
      2014-03-28
  • [Presentation] Enantioselective Synthesis of Paracyclophanes and Their Application as Chiral Ligands2013

    • Author(s)
      Shibata, T. ; Kanda, K.; Oshima, S.
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2013
    • Place of Presentation
      北京(中国)
    • Year and Date
      2013-12-04
    • Invited
  • [Presentation] Enantioselective Synthesis of Paracyclophanes and Their Application2013

    • Author(s)
      Shibata, T. ; Kanda, K.; Oshima, S.
    • Organizer
      IUPAC 9th International Conference on Novel Materials and their Synthesis
    • Place of Presentation
      上海(中国)
    • Year and Date
      2013-10-19
    • Invited
  • [Presentation] Consecutive Inter- and Intramolecular [2+2+2] Cycloadditions of Triynes for the Synthesis of Macrocyclic Heteroarylene2013

    • Author(s)
      柴田 高範, 藤本 雅 子, 大 谷 卓
    • Organizer
      14th European Symposium on Organic Reactivity
    • Place of Presentation
      プラハ(チェコ)
    • Year and Date
      2013-09-02
  • [Presentation] Synthesis of Macrocyclic Heteroarylenes by Consecutive Inter- and Intramolecular Cycloadditions2013

    • Author(s)
      柴田 高範, 藤本 雅子, 大谷 卓
    • Organizer
      Asian Chemical Congress
    • Place of Presentation
      シンガポール(シンガポール)
    • Year and Date
      2013-08-19
  • [Presentation] 不斉オルトリチオ化を利用した [n] パラシクロファン骨格を有する新規面不斉リン配位子の合成とパラジウム触媒を用いた不斉カップリングへの応用2013

    • Author(s)
      大嶋 祥也, 濵中 理紗, 神田 和正, 柴田 高範
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Year and Date
      2013-03-23
  • [Presentation] 不斉薗頭カップリング反応による面不斉を有するパラシクロファンの高エナンチオ選択的合成2013

    • Author(s)
      濵中 理紗, 神田 和正, 柴田 高範
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Year and Date
      2013-03-23
  • [Presentation] 連続的[2+2+2]付加環化反応を利用したチオフェンを含む環状ヘテロアリレン骨格の構築2013

    • Author(s)
      藤本 雅子, 大谷 卓, 柴田 高範
    • Organizer
      日本化学会第93春季年会
    • Place of Presentation
      立命館大学(滋賀)
    • Year and Date
      2013-03-23
  • [Presentation] Synthesis of Cyclic Polyarylenes by Consecutive Cycloadditions2013

    • Author(s)
      Shibata, T
    • Organizer
      The 4th Symposium on Chiral Science & Technology
    • Place of Presentation
      東京
    • Year and Date
      2013-03-01
    • Invited
  • [Presentation] New Approach to the Enantioselective Synthesis of Paracyclophanes2012

    • Author(s)
      Shibata, T.
    • Organizer
      Cambodian Malaysian Chemical Conference (CMCC)
    • Place of Presentation
      Siem Reap (Cambodia)
    • Year and Date
      2012-10-19
    • Invited
  • [Presentation] Enantioselective Synthesis of Cyclic Polyarylenes by Consecutive Cycloadditions2012

    • Author(s)
      Shibata, T.
    • Organizer
      IUPAC 8th International Conference on Novel Materials and their Synthesis, IUPAC 8th International Conference on Novel Materials and their Synthesis
    • Place of Presentation
      西安(中国)
    • Year and Date
      2012-10-15
    • Invited
  • [Presentation] 面不斉パラシクロファンの高エナンチオ選択的合成法の開発2012

    • Author(s)
      神田 和正, 濱中 理紗, 小池 珠美, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應大学(神奈川)
    • Year and Date
      2012-03-28
  • [Presentation] 不斉オルトリチオ化を利用した[n]パラシクロファン骨格を有する新規不斉リン配位子の合成と応用2012

    • Author(s)
      濱中 理紗,神田 和正,遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應大学(神奈川)
    • Year and Date
      2012-03-28
  • [Presentation] 連続的[2+2+2]付加環化反応を利用したヘテロ芳香環を含む環状ポリアリレン骨格の構築2012

    • Author(s)
      藤本 雅, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應大学(神奈川)
    • Year and Date
      2012-03-26
  • [Presentation] アレーンルテニウム錯体を用いた触媒反応開発2012

    • Author(s)
      大塚 麻依子, 横山 裕也, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應大学(神奈川)
    • Year and Date
      2012-03-25
  • [Presentation] η6アレーンルテニウム錯体を経由するα-置換スチレンへの触媒的不斉求核付加反応2012

    • Author(s)
      横山 裕也, 大塚 麻依子, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶應大学(神奈川)
    • Year and Date
      2012-03-25
  • [Presentation] Synthesis of cyclic polyphenylenes using consecutive [2+2+2] cycloadditions2011

    • Author(s)
      Shibata, T.
    • Organizer
      14th Asian Chemical Congress
    • Place of Presentation
      バンコク, タイ
    • Year and Date
      2011-09-06
    • Invited
  • [Presentation] New Strategy for the Construction of Cyclic Polyphenylenes by Consecutive [2+2+2] Cycloaddition2011

    • Author(s)
      Shibata, T .; Fujimoto, M.; Hirashima, H.; Chiba, T.; Endo, K.
    • Organizer
      4th International Symposium on Advances in Synthetic and Medicinal Chemistry
    • Place of Presentation
      サンクトペテルブルグ, ロシア
    • Year and Date
      2011-08-24
  • [Presentation] エナンチオ選択的オルトリチオ化を利用した新規な面不斉パラシクロファン骨格の創製2011

    • Author(s)
      神田 和正, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-29
  • [Presentation] 分子間,分子内[2+2+2]付加環化反応を利用したシロール環を含むヘリセンのエナンチオ選択的合成2011

    • Author(s)
      内山 理文, 吉浪 雄亮, 土釜 恭直, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-29
  • [Presentation] η6-ベンゼンルテニウム錯体を用いた不活性フルオロアレーンと環状アミンの効率的な触媒的芳香族求核置換反応2011

    • Author(s)
      横山 裕也, 大塚 麻依子, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-29
  • [Presentation] 連続的[2+2+2]付加環化反応を利用したヘキサフェニレン骨格の構築2011

    • Author(s)
      藤本 雅子, 平島 裕之, 千羽 達也, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-29
  • [Presentation] 分子内[2+2+2]付加環化反応を利用したピリジノファンの高エナンチオ選択的合成2011

    • Author(s)
      三好 真由, 内山 理文, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-29
  • [Presentation] スチレンクロム錯体に対する逆マルコフニコフ型アルコキシ化2011

    • Author(s)
      大塚 麻依子, 遠藤 恆平, 柴田 高範
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(神奈川)
    • Year and Date
      2011-03-26
  • [Presentation] Construction of New Chiral Cyclic Skeletons Based on the Enantioselective [2+2+2] Cycloaddition2010

    • Author(s)
      Shibata, T
    • Organizer
      7th Symposium on Chemical Approaches to Chirality
    • Place of Presentation
      東京理科大学, 東京
    • Year and Date
      2010-09-29
    • Invited
  • [Presentation] Enantioselective Construction of New Chiral Cyclic Scaffolds Using [2+2+2] Cycloaddition2010

    • Author(s)
      Shibata, T
    • Organizer
      18th International Conference on Organic Synthesis (ICOS18)
    • Place of Presentation
      ベルゲン, ノルウェー
    • Year and Date
      2010-08-02
  • [Presentation] 触媒的不斉付加環化反応の新展開2010

    • Author(s)
      柴田 高範
    • Organizer
      ファインケミカルズ合成触媒のフロンティア
    • Place of Presentation
      東京農工大学, 東京
    • Year and Date
      2010-06-05
    • Invited
  • [Presentation] Enantioselective Synthesis of Axially Chiral Polyaryls using Ir-catalyzed [2+2+2] Cycloaddition2010

    • Author(s)
      Shibata, T
    • Organizer
      1st Annual World Congress of Catalytic Asymmetric Synthesis-2010
    • Place of Presentation
      北京, 中国
    • Year and Date
      2010-05-21
    • Invited
  • [Remarks]

    • URL

      http://www.chem.waseda.ac.jp/shibata/

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Published: 2015-06-25  

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