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Development of Highly Electron-Accepting Diphosphene Ligands and Application to the Synthesis of Helical Molecules in Optically Active Form

Research Project

Project/Area Number 16H07126
Research Category

Grant-in-Aid for Research Activity Start-up

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionOsaka Prefecture University

Principal Investigator

Tsurusaki Akihiro  大阪府立大学, 理学(系)研究科(研究院), 助教 (40623848)

Project Period (FY) 2016-08-26 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Fiscal Year 2017: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2016: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Keywordsリン / ジホスフェン / 遷移金属錯体 / 触媒反応 / 軸不斉 / 光学活性 / 1,1’-ビナフチル / 金 / 遷移金属 / 有機合成化学 / 電子受容性配位子 / 分子内環化反応
Outline of Final Research Achievements

We succeeded in the synthesis of the new diphosphene having the P=P double-bond, which is expected to have the high electron-accepting character, and 1,1’-binaphthyl group with the axial chirality in both racemic and enantiomerically pure forms. Spectroscopic analyses, X-ray crystallographic analysis, and theoretical calculations revealed their structures, properties, and isomerization behavior among four stereoisomers. Furthermore, the corresponding diphosphene-gold(I) complex was isolated and utilized as a catalyst for the intramolecular hydroarylation reaction of aryl butynyl ether.

Report

(3 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Annual Research Report
  • Research Products

    (20 results)

All 2018 2017 2016

All Journal Article (5 results) (of which Peer Reviewed: 5 results) Presentation (15 results) (of which Int'l Joint Research: 2 results)

  • [Journal Article] 1,1’-Binaphthyl-substituted Diphosphene: Synthesis, Structures, and Chiral Optical Properties2018

    • Author(s)
      Tsurusaki, A.; Ura, R.; Kamikawa, K.
    • Journal Title

      Dalton Trans.

      Volume: 47 Issue: 13 Pages: 4437-4441

    • DOI

      10.1039/c8dt00441b

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Syntehsis, Structures, and Properties of Hexapole Helicenes: Assembling Six [5]Helicene Substructures into Highly Twisted Aromatic Systems2017

    • Author(s)
      Hosokawa, T.; Takahashi, Y.; Matsushima, T.; Watanabe, S.; Kikkawa, S.; Azumaya, I.; Tsurusaki, A.; Kamikawa, K.
    • Journal Title

      J. Am Chem. Soc.

      Volume: 139 Issue: 51 Pages: 18512-18521

    • DOI

      10.1021/jacs.7b07113

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis and structures of lithium alkoxytris(dimethylphenylsilyl)borates2017

    • Author(s)
      Akihiro Tsurusaki, Keisuke Yoshida, Soichiro Kyushin
    • Journal Title

      Dalton Trans.

      Volume: 46 Issue: 27 Pages: 8705-8708

    • DOI

      10.1039/c7dt00395a

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis, Structures, and Electronic Properties of Dithienosiloles Bearing Bulky Aryl Groups: Conjugation between a pi-Electron System and “Perpendicular” Aryl Groups2017

    • Author(s)
      Akihiro Tsurusaki, Atsushi Kobayashi, Soichiro Kyushin
    • Journal Title

      Asian. J. Org. Chem.

      Volume: 6 Issue: 6 Pages: 737-745

    • DOI

      10.1002/ajoc.201700058

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Decasilahexahydrotriquinacene and Decasilaisotwistane: σConjugation on a Bowl Surface2017

    • Author(s)
      Akihiro Tsurusaki, Yu Koyama, Soichiro Kyushin
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 139 Issue: 11 Pages: 3982-3985

    • DOI

      10.1021/jacs.7b00250

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed
  • [Presentation] [5]および[7]ヘリセン構造を有する六重ヘリセンに関する合成、および理論化学的考察2018

    • Author(s)
      細川 朋佳・麻田 俊雄・津留崎 陽大・神川 憲
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 軸不斉ビナフチル置換ジホスフェンの光学特性2018

    • Author(s)
      浦 里華子・津留崎 陽大・神川 憲
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 面不斉金属錯体を基盤とするホスフィン‐オレフィン配位子の合成と不斉触媒反応への応用2018

    • Author(s)
      大矢 直輝・曾 雅怡・津留崎 陽大・神川 憲
    • Organizer
      日本化学会第98春季年会(2018)
    • Related Report
      2017 Annual Research Report
  • [Presentation] 1,1'-ビナフチル置換ジホスフェンの合成2017

    • Author(s)
      浦 里華子・津留崎 陽大・神川 憲
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] [5]ヘリセン誘導体の[2+2+2]環化三量化反応による六重ヘリセンの合成と物性2017

    • Author(s)
      細川朋佳・津留崎陽大・神川憲
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 6 つの[5]ヘリセン骨格を持つ六重ヘリセンの熱異性化挙動2017

    • Author(s)
      細川朋佳・津留崎陽大・神川憲
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 面不斉金属錯体を基盤とするホスフィン‐オレフィン配位子の合成と不斉触媒反応への応用2017

    • Author(s)
      大矢 直輝・曾 雅怡・津留崎 陽大・神川 憲
    • Organizer
      日本化学会第97春季年会(2017)
    • Place of Presentation
      慶應義塾大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] 大きなねじれ構造を有する六重ヘリセンの合成、および物性2017

    • Author(s)
      細川朋佳・高橋裕輔・松島智也・吉川晶子・東屋功・渡邊総一郎・津留崎陽大・神川憲
    • Organizer
      第28回基礎有機化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 1,1'-ビナフチル置換ジホスフェンとその金(I)錯体の合成と構造2017

    • Author(s)
      浦 里華子・津留崎 陽大・神川 憲
    • Organizer
      第64回有機金属化学討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 面不斉ハーフメタロセン配位子を活用した不斉触媒反応2017

    • Author(s)
      大矢直輝・曽雅怡・津留崎陽大・神川憲
    • Organizer
      第120回触媒討論会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 1,1'-ビナフチル置換ジホスフェンと錯形成2017

    • Author(s)
      浦 里華子・津留崎 陽大・神川 憲
    • Organizer
      第7回CSJ化学フェスタ2017
    • Related Report
      2017 Annual Research Report
  • [Presentation] Synthesis and Structures of 1,1’-Binaphthyl-Substituted Diphosphene and its Gold(I) Complex2017

    • Author(s)
      Rikako Ura, Akihiro Tsurusaki, Ken Kamikawa
    • Organizer
      Joint Symposium of Asia Five Universities
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and Properties of Hexapole Helicenes with Highly Distorted Structures2017

    • Author(s)
      Tomoka Hosokawa, Yusuke Takahashi, Tomoya Matsushima, Soichiro Watanabe, Shoko Kikkawa, Isao Azumaya, Akihiro Tsurusaki, Ken Kamikawa
    • Organizer
      Joint Symposium of Asia Five Universities
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis of Binaphthyl-Substituted Diphosphenes2016

    • Author(s)
      Rikako Ura, Akihiro Tsurusaki, Ken Kamikawa
    • Organizer
      The 3rd Joint Symposium of NTUT, NTNU, and OPU on Chemistry
    • Place of Presentation
      Osaka Prefecture University, I-site Namba
    • Year and Date
      2016-09-05
    • Related Report
      2016 Annual Research Report
  • [Presentation] Synthesis of Hexapole Helicenes by Palladium-Catalyzed [2+2+2] Cyclization Reactions2016

    • Author(s)
      Tomoka Hosokawa, Akihiro Tsurusaki, Ken Kamikawa
    • Organizer
      The 3rd Joint Symposium of NTUT, NTNU, and OPU on Chemistry
    • Place of Presentation
      Osaka Prefecture University, I-site Namba
    • Year and Date
      2016-09-05
    • Related Report
      2016 Annual Research Report

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Published: 2016-09-02   Modified: 2019-03-29  

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