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Oxidative Carbon-Carbon Coupling Reactions Using Organocatalysis

Research Project

Project/Area Number 25620078
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionNagoya University

Principal Investigator

UYANIK Muhammet  名古屋大学, 工学(系)研究科(研究院), 助教 (20452188)

Project Period (FY) 2013-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2013: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Keywords合成化学 / 有機化学 / 酸化的カップリング / ビアリール / アリールキノン
Research Abstract

Biaryl compounds and arylquinones are key skeletons of many biologically active compounds and functional organic materials. The efficient and environmentally benign synthetic method for those compounds is required. We succeeded in oxidative biaryl coupling reaction of substituted phenols or naphthols catalyzed by hypoiodite salts, which were generated in situ from the corresponding iodide and aqueous hydrogen peroxide as a co-oxidant. The corresponding biphenols or binaphthols were obtained in moderate to high yields. Additionally, depending on the substrates, diphenoquinones or dinaphthoquinones were also obtained by further oxidations. Moreover, we succeeded in hypoiodite-catalyzed oxidation of hydroquinones to quinones with aqueous hydrogen peroxide. The subsequent one-pot cross coupling of these quinones with aryl compounds could be achieved catalyzed by alkali or alkaline earth metal bulky borate salts to give the corresponding arylquinones in good yields.

Report

(2 results)
  • 2013 Annual Research Report   Final Research Report ( PDF )
  • Research Products

    (8 results)

All 2014 2013 Other

All Presentation (4 results) Remarks (2 results) Patent(Industrial Property Rights) (2 results)

  • [Presentation] ヒドロキノンのタンデム型ワンポット酸化/クロスカップリング反応によるアリールキノンの合成2014

    • Author(s)
      永田大, UYANIK Muhammet, 石原一彰
    • Organizer
      日本化学会第94回春季年会
    • Place of Presentation
      名古屋大学, 愛知県
    • Related Report
      2013 Final Research Report
  • [Presentation] ヒドロキノンのタンデム型ワンポット酸化/クロスカップリング反応によるアリールキノンの合成2014

    • Author(s)
      永田大、UYANIK Muhammet、石原一彰
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学、愛知県
    • Related Report
      2013 Annual Research Report
  • [Presentation] (次)亜ヨウ素酸塩触媒によるフェノール類の酸化的ビアリールカップリング反応2013

    • Author(s)
      永田大, UYANIK Muhammet, 石原一彰
    • Organizer
      第48回有機反応若手の会
    • Place of Presentation
      デュープレックスセミナーホテル, 茨城県
    • Related Report
      2013 Final Research Report
  • [Presentation] (次)亜ヨウ素酸塩触媒によるフェノール類の酸化的ビアリールカップリング反応2013

    • Author(s)
      永田大、UYANIK Muhammet、石原一彰
    • Organizer
      第48回有機反応若手の会
    • Place of Presentation
      デュープレックス、茨城県
    • Related Report
      2013 Annual Research Report
  • [Remarks]

    • URL

      http://www.ishihara-lab.net/

    • Related Report
      2013 Final Research Report
  • [Remarks] http://www.ishihara-lab.net/

    • Related Report
      2013 Annual Research Report
  • [Patent(Industrial Property Rights)] アリールヒドロキノン類の製法及びアリールキノン類の製法2014

    • Inventor(s)
      石原一彰, UYANIK Muhammet
    • Industrial Property Rights Holder
      国立大学法人名古屋大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014-03-10
    • Related Report
      2013 Final Research Report
  • [Patent(Industrial Property Rights)] アリールヒドロキノン類の製法及びアリールキノン類の製法2014

    • Inventor(s)
      石原一彰、UYANIK Muhammet
    • Industrial Property Rights Holder
      国立大学法人名古屋大学
    • Industrial Property Rights Type
      特許
    • Filing Date
      2014
    • Related Report
      2013 Annual Research Report

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Published: 2014-07-25   Modified: 2021-04-07  

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