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Organocatalytic Deprotonation Reaction Using Onium Amide

Research Project

Project/Area Number 23659001
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeMulti-year Fund
Research Field Chemical pharmacy
Research InstitutionTohoku University

Principal Investigator

KONDO Yoshinori  東北大学, 大学院・薬学研究科, 教授 (90162122)

Project Period (FY) 2011 – 2012
Project Status Completed (Fiscal Year 2012)
Budget Amount *help
¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000)
Fiscal Year 2012: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords有機反応学 / 分子活性化 / 分子変換 / 有機触媒 / オニウムアミド / 脱プロトン化 / 芳香族複素環 / 不斉変換 / 芳香複素環 / 脱プロトン / ホスファゼニウム / 官能基選択性 / 部位選択性
Research Abstract

Organocatalytic process has been regarded to be attractive from viewpoints of selectivity, safety, and sustainability, and the development of organocatalytic processes for deprotonative functionalization of aromatics and heteroaromatics is considered to be one of highly challenging subjects in organic synthesis. We have been working on organocatalytic transformation of aromatic and heteroaromatic compounds, and we developed a simple catalytic deprotonative functionalization of heteroaromatic ring under metal-free mild conditions using onium amides, generated in situ from the combination of aminosilanes and onium fluorides, as bases.

Report

(3 results)
  • 2012 Annual Research Report   Final Research Report ( PDF )
  • 2011 Research-status Report
  • Research Products

    (20 results)

All 2013 2012 2011 Other

All Journal Article (9 results) (of which Peer Reviewed: 9 results) Presentation (9 results) Remarks (2 results)

  • [Journal Article] Organocatalytic deprotonative functionalization of C(sp2)-H and C(sp3)-H bonds using in situ generated onium amide2012

    • Author(s)
      K. Inamoto, H. Okawa, H. Taneda, M. Sato, Y. Hirono, M. Yonemoto, Y. Kondo
    • Journal Title

      Chemical Communications

      Volume: 48 Issue: 78 Pages: 9771-9773

    • DOI

      10.1039/c2cc35701a

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Palladium-catalyzed C-H cyclization in water: a milder route to2-arylbenzothiazoles2012

    • Author(s)
      Kiyofumi Inamoto, Kanako Nozawa, Yoshinori Kondo
    • Journal Title

      Synlett

      Volume: 23 Issue: 11 Pages: 1678-1682

    • DOI

      10.1055/s-0031-1291164

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Efficient useof a surfactant for copper-catalyzed coupling reaction of arylboronic acids with imidazoles in water2012

    • Author(s)
      Kiyofumi Inamoto, Kanako Nozawa, JunKadokawa, Yoshinori Kondo
    • Journal Title

      Tetrahedron

      Volume: 68 Issue: 38 Pages: 7794-7798

    • DOI

      10.1016/j.tet.2012.07.042

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 3-carboxylated indoles through a tandem process involving cyclization of 2-ethynylanilines followed by CO2 fixation in the absence of transition metal catalysists2012

    • Author(s)
      K. Inamoto, N. Asano, Y. Nakamura, M. Yonemoto, Y. Kondo
    • Journal Title

      Organic Letters

      Volume: 14 Issue: 10 Pages: 2622-2625

    • DOI

      10.1021/ol300958c

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] A copper-based catalytic system for carboxylation of terminal alkynes: synthesis of alkyl 2-alkynoates2012

    • Author(s)
      K. Inamoto, N. Asano, K. Kobayashi, M. Yonemoto, Y. Kondo
    • Journal Title

      Organic & Biomelecular Chemistry

      Volume: 10 Issue: 8 Pages: 1514-1516

    • DOI

      10.1039/c2ob06884b

    • Related Report
      2012 Annual Research Report 2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Synthesis of 3-carboxylated indoles through a tandem process involving cyclization of 2-ethynylanilines followed by CO2 fixation in the absence of transition metal catalysts2012

    • Author(s)
      K. Inamoto, N. Asano, Y. Nakamura, M. Yonemoto, Y. Kondo
    • Journal Title

      Organic Letters

      Volume: 14 Pages: 2622-2625

    • Related Report
      2012 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Micellar system in copper-catalyzed hydroxylation of arylboronic acids : facile access to phenols2011

    • Author(s)
      K.Inamoto, K.Nozawa, M.Yonemoto, Y.Kondo
    • Journal Title

      Chemical Communications

      Volume: 47 Issue: 42 Pages: 11775-11777

    • DOI

      10.1039/c1cc14974a

    • Related Report
      2012 Final Research Report
    • Peer Reviewed
  • [Journal Article] Micellar system in copper-catalyzed hydroxylation of arylboronic acids: facile access to phenols2011

    • Author(s)
      Kiyofumi Inamoto, Kanako Nozawa, Misato Yonemoto, Yoshinori Kondo
    • Journal Title

      Chemical Communications

      Volume: 47 Pages: 11775-11777

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Journal Article] Functionalization of heteroaromatic N-oxides using organic superbase catalyst2011

    • Author(s)
      Yuta Araki, Koji Kobayashi, Misato Yonemoto, Yoshinori Kondo
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 9 Pages: 78-80

    • Related Report
      2011 Research-status Report
    • Peer Reviewed
  • [Presentation] オニウムアミド塩基を用いたc(SP3)-H脱プロトン化-修飾反応の開発2013

    • Author(s)
      稲本浄文、種田宏、吉川晶子、根東義則
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      横浜
    • Related Report
      2012 Final Research Report
  • [Presentation] オニウムアミドを用いたC(sp3)-H脱プロトン化ー修飾反応の開発2013

    • Author(s)
      稲本浄文、種田宏、吉川晶子、根東義則
    • Organizer
      日本薬学会第133年会
    • Place of Presentation
      パシフィコ横浜
    • Related Report
      2012 Annual Research Report
  • [Presentation] フッ化オニウムによるアミノシランの活性化を介した芳香複素環の修飾反応2012

    • Author(s)
      大川ひとみ、廣野佑太郎、米本みさと、吉川晶子、稲本浄文、根東義則
    • Organizer
      第51回日本薬学会東北支部大会
    • Place of Presentation
      青森
    • Year and Date
      2012-10-07
    • Related Report
      2012 Final Research Report
  • [Presentation] フッ化物の添加による有機亜鉛試薬の活性化反応2012

    • Author(s)
      藤村英範、米本みさと、吉川晶子、稲本浄文、根東義則
    • Organizer
      第51回日本薬学会東北支部大会
    • Place of Presentation
      青森
    • Year and Date
      2012-10-07
    • Related Report
      2012 Final Research Report
  • [Presentation] オニウムアミド塩基による触媒的脱プロトン化-修飾反応の開発2012

    • Author(s)
      稲本浄文、大川ひとみ、佐藤菜央美、種田宏、廣野佑太郎、米本みさと、吉川晶子、根東義則
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      東京
    • Related Report
      2012 Final Research Report
  • [Presentation] オニウムアミド塩基による触媒的脱プロトン化-修飾反応の開発2012

    • Author(s)
      稲本浄文、大川ひとみ、佐藤菜央美、種田宏、廣野佑太郎、米本みさと、吉川晶子、根東義則
    • Organizer
      第38回反応と合成の進歩シンポジウム
    • Place of Presentation
      タワーホール船堀
    • Related Report
      2012 Annual Research Report
  • [Presentation] フッ化オニウムによるアミノシランの活性化を介した芳香族複素環の修飾反応

    • Author(s)
      大川ひとみ、廣野佑太郎、米本みさと、吉川晶子、稲本浄文、根東義則
    • Organizer
      第51回日本薬学会東北支部大会
    • Place of Presentation
      青森大学薬学部
    • Related Report
      2012 Annual Research Report
  • [Presentation] オニウム塩触媒を用いる選択的分子変換反応

    • Author(s)
      米本みさと、荒木勇太、廣野佑太郎、大川ひとみ、佐藤菜央美、稲本浄文、根東義則
    • Organizer
      第37回反応と合成の進歩シンポジウム
    • Place of Presentation
      徳島
    • Related Report
      2011 Research-status Report
  • [Presentation] 二酸化炭素を用いたシクロカルボキシル化を経由する複素環合成

    • Author(s)
      浅野成美、稲本浄文、米本みさと、根東義則
    • Organizer
      第41回複素環化学討論会
    • Place of Presentation
      熊本
    • Related Report
      2011 Research-status Report
  • [Remarks]

    • URL

      http://www.pharm.tohoku.ac.jp/~henkan/lab/henkan_top.html

    • Related Report
      2012 Final Research Report
  • [Remarks] 分子変換化学分野

    • URL

      http://www.pharm.tohoku.ac.jp/~henkan/lab/henkan_top.html

    • Related Report
      2012 Annual Research Report

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Published: 2011-08-05   Modified: 2019-07-29  

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