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Syntheis of novel binaphthol derivatives via remote C-H funcionalization

Research Project

Project/Area Number 15K17859
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Research InstitutionNara National College of Technology

Principal Investigator

Kamei Toshiyki  奈良工業高等専門学校, 物質化学工学科, 准教授 (70534452)

Project Period (FY) 2015-04-01 – 2017-03-31
Project Status Completed (Fiscal Year 2016)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2015: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
KeywordsC-H官能基化 / p型半導体 / ペリキサンテノキサンテン / 銅触媒 / 空気酸化 / C-H環化反応 / ペリキサンテノキサンテンビスイミド / p型半導体材料 / n型半導体材料 / 多環芳香族化合物 / C-H結合活性化 / 有機半導体材料
Outline of Final Research Achievements

Metal-catalyzed functionalization at 8 position of binaphthol proceeded. However, the intramolecular cyclization with hydroxy group was much faster than intermolecular reactions to afford peri-xanthenoxanthene (PXX) preferentially.
Since practical synthesis of PXX did not reported so far, the study was focused on the development of this intramolecular cyclization. As a result, efficient synthesis of PXX was developed using air as the reoxidant.
I disclosed that radical cation of newly synthesized PXX derivatives was found very stable from electrochemical analysis.

Report

(3 results)
  • 2016 Annual Research Report   Final Research Report ( PDF )
  • 2015 Research-status Report
  • Research Products

    (7 results)

All 2017 2016 2015

All Journal Article (1 results) (of which Peer Reviewed: 1 results,  Acknowledgement Compliant: 1 results) Presentation (5 results) (of which Int'l Joint Research: 1 results) Patent(Industrial Property Rights) (1 results)

  • [Journal Article] Cu-Catalyzed Aerobic Oxidative C-H/C-O Cyclization of 2,2'-Binaphthols: Practical Synthesis of PXX Derivatives2017

    • Author(s)
      Toshiyuki Kamei, Mizuho Uryu, Toyoshi Shimada
    • Journal Title

      Organic Letters

      Volume: 印刷中 Issue: 10 Pages: 2714-2717

    • DOI

      10.1021/acs.orglett.7b01060

    • Related Report
      2016 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] u-Catalyzed Oxidative Coupling-Cyclization for peri-Xanthenoxanthene Bisimide (PXXBI) Derivatives and Their Properties2017

    • Author(s)
      Toshiyuki Kamei, Shiori Kimura, Nobuhiko Takeuchi, Toyoshi Shimada
    • Organizer
      日本化学会年会
    • Place of Presentation
      慶応大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Annual Research Report
  • [Presentation] Cu-Catalyzed Oxidative Coupling-Cyclization for peri-Xanthenoxanthene Bisimide (PXXBI) Derivatives2016

    • Author(s)
      Toshiyuki Kamei, Shiori Kimura, Nobuhiko Takeuchi, Toyoshi Shimada
    • Organizer
      C&FC2016
    • Place of Presentation
      howard civil service international house, Taipei
    • Year and Date
      2016-11-10
    • Related Report
      2016 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Cu-catalyzed oxidative C-H/C-O cyclization of binaphthols using air as the sole oxidant: Efficient synthesis of PXX derivatives2015

    • Author(s)
      Toshiyuki Kamei, Mizuho Uryu, Toyoshi Shimada
    • Organizer
      Pacifichem2015
    • Place of Presentation
      ハワイコンベンションセンター
    • Year and Date
      2015-12-19
    • Related Report
      2015 Research-status Report
  • [Presentation] Cu-Catalyzed Aerobic Oxidative C-H Functionalization/C-O Cyclization of 2,2’-Binaphthols; Efficient Synthesis of PXX Derivatives2015

    • Author(s)
      Toshiyuki Kamei, Mizuho Uryu, Toyoshi Shimada
    • Organizer
      IKCOC13
    • Place of Presentation
      リーガロイヤルホテル京都
    • Year and Date
      2015-11-12
    • Related Report
      2015 Research-status Report
  • [Presentation] 空気中の酸素を再酸化剤として用いた銅触媒によ る酸化的 C-H 活性化/C-O 環化反応:効率的PXX誘 導体合成法の開発2015

    • Author(s)
      亀井稔之、瓜生瑞穂、嶋田豊司
    • 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
    • Year and Date
      2015-09-09
    • Related Report
      2015 Research-status Report
  • [Patent(Industrial Property Rights)] ペリキサンテノキサンテンビスイミド化合物、その製造方法、有機EL素子、有機薄膜太陽電池2016

    • Inventor(s)
      亀井稔之、高松嘉則、竹中直巳
    • Industrial Property Rights Holder
      亀井稔之、高松嘉則、竹中直巳
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-170281
    • Filing Date
      2016-08-31
    • Related Report
      2016 Annual Research Report

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Published: 2015-04-16   Modified: 2018-12-17  

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