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Development of a novel method to generate nitrogen-centered radical species and its application to amination reactions

Research Project

Project/Area Number 16K17868
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Organic chemistry
Research InstitutionOsaka University

Principal Investigator

Kiyokawa Kensuke  大阪大学, 工学研究科, 助教 (80632364)

Project Period (FY) 2016-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2017: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords超原子価ヨウ素 / ヨウ素 / アミノ化 / ラジカル / 有機化学 / 合成化学
Outline of Final Research Achievements

In the presence of a metal catalyst, the amination of a C-H bond of aromatic compounds by a nitrogen-centered radical species generated from a hypervalent iodine reagent containing a phthalimidate proceeded to afford aniline derivatives albeit in low yield. In addition, an amination of enol silyl ether derived from various ketones proceeded effectively to provide α-aminated ketones in good yields. These results demonstrate a novel reactivity of hypervalent iodine reagents containing a phthalimidate.

Report

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

    (26 results)

All 2018 2017 2016

All Journal Article (6 results) (of which Peer Reviewed: 6 results,  Open Access: 1 results,  Acknowledgement Compliant: 2 results) Presentation (20 results) (of which Int'l Joint Research: 3 results)

  • [Journal Article] Oxidative Cyclization of β,γ-Unsaturated Carboxylic Acids Using Hypervalent Iodine Reagents: An Efficient Synthesis of 4-Substituted Furan-2-ones2017

    • Author(s)
      Kiyokawa Kensuke、Minakata Satoshi、Takemoto Kenta、Yahata Shunsuke、Kojima Takumi
    • Journal Title

      Synthesis

      Volume: 49 Issue: 13 Pages: 2907-2912

    • DOI

      10.1055/s-0036-1588987

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed
  • [Journal Article] Hypervalent Iodine(III)-Mediated Decarboxylative Ritter-Type Amination Leading to the Production of α-Tertiary Amine Derivatives2017

    • Author(s)
      Kiyokawa Kensuke、Watanabe Tomoki、Fra Laura、Kojima Takumi、Minakata Satoshi
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 22 Pages: 11711-11720

    • DOI

      10.1021/acs.joc.7b01202

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Activation of 1-Cyano-3,3-dimethyl-3-(1H)-1,2-benziodoxole with B(C6F5)3 Enabling the Electrophilic Cyanation of Silyl Enol Ethers2017

    • Author(s)
      Nagata Takaya、Matsubara Hiroki、Kiyokawa Kensuke、Minakata Satoshi
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 17 Pages: 4672-4675

    • DOI

      10.1021/acs.orglett.7b02313

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Recent Advances in the Synthesis of β-Ketonitriles2017

    • Author(s)
      Kiyokawa Kensuke、Minakata Satoshi、Nagata Takaya
    • Journal Title

      Synthesis

      Volume: 50 Issue: 03 Pages: 485-498

    • DOI

      10.1055/s-0036-1589128

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Ritter-Type Amination of C-H Bonds at Tertiary Carbon Centers Using Iodic Acid as an Oxidant2016

    • Author(s)
      Kensuke Kiyokawa, Kenta Takemoto, and Satoshi Minakata
    • Journal Title

      Chemical Communications

      Volume: 52 Issue: 89 Pages: 13082-13085

    • DOI

      10.1039/c6cc07164c

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Electrophilic Cyanation of Boron Enolates: Efficient Access to Various β-Ketonitrile Derivatives2016

    • Author(s)
      Kensuke Kiyokawa, Takaya Nagata, and Satoshi Minakata
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 55 Issue: 35 Pages: 10458-10462

    • DOI

      10.1002/anie.201605445

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 単体ヨウ素/超原子価ヨウ素系を活用したカルボン酸の脱炭酸酸素官能基化2018

    • Author(s)
      奥松大地,清川謙介,南方聖司
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ヨウ素酸化剤を活用する第三級C-H結合の酸素官能基化2018

    • Author(s)
      清川謙介,伊東 亮, 南方聖司
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 次亜ヨウ素酸tert-ブチルを活用したスルファマートエステルを窒素源とするオレフィン類のアジリジン化2018

    • Author(s)
      中村彰悟,清川謙介, 南方聖司
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 超原子価ヨウ素試剤を利用する脱炭酸リッター型アミノ化反応2017

    • Author(s)
      渡部友貴、清川謙介、南方聖司
    • Organizer
      日本化学会第97春季年会
    • 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 Research-status Report
  • [Presentation] Ritter-Type Amination of C-H Bonds at Tertiary Carbon Centers Using Iodic Acid as an Oxidant2017

    • Author(s)
      Kensuke Kiyokawa, Kenta Takemoto, Satoshi Minakata
    • Organizer
      日本化学会第97春季年会
    • 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 Research-status Report
  • [Presentation] 五酸化二ヨウ素を活用する第三級C-H結合の酸素官能化2017

    • Author(s)
      伊東 亮、竹本憲太、清川謙介、南方聖司
    • Organizer
      日本化学会第97春季年会
    • 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 Research-status Report
  • [Presentation] 次亜ヨウ素酸tert-ブチルを活用したスルファマートエステルの分子内C-Hアミノ化反応2017

    • Author(s)
      岩井田晃次、清川謙介、南方聖司
    • Organizer
      日本化学会第97春季年会
    • 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 Research-status Report
  • [Presentation] Electrophilic Cyanation of Boron Enolates2017

    • Author(s)
      Takaya Nagata, Kensuke Kiyokawa, Satoshi Minakata
    • Organizer
      日本化学会第97春季年会
    • 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 Research-status Report
  • [Presentation] N-ヒドロキシフタルイミド触媒を利用する第三級炭素のメタルフリー官能基化2017

    • Author(s)
      清川謙介, 伊東 亮, 竹本憲太, 南方聖司
    • Organizer
      第10回 有機触媒シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 超原子価ヨウ素/単体ヨウ素系を活用するカルボン酸の脱炭酸官能基化2017

    • Author(s)
      奥松大地, 清川謙介, 南方聖司
    • Organizer
      第7回CSJ化学フェスタ
    • Related Report
      2017 Annual Research Report
  • [Presentation] 五酸化二ヨウ素を酸化剤として活用する第三級C-H結合の酸素官能化2017

    • Author(s)
      伊東 亮, 清川謙介, 南方聖司
    • Organizer
      第20回ヨウ素学会シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 次亜ヨウ素酸tert-ブチルを活用したスルファマートエステルの分子内C-Hアミノ化2017

    • Author(s)
      岩井田晃次, 清川謙介, 南方聖司
    • Organizer
      第37回有機合成若手セミナー「明日の有機合成を担う人のために」
    • Related Report
      2017 Annual Research Report
  • [Presentation] ヨウ素酸化剤を活用する第三級C-H結合酸素官能化反応2017

    • Author(s)
      伊東 亮, 清川謙介, 南方聖司
    • Organizer
      第6回 JACI/GSCシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] ヨウ素酸を酸化剤として用いる第三級C-H結合のリッター型アミノ化2016

    • Author(s)
      竹本憲太、清川謙介、南方聖司
    • Organizer
      第43回有機典型元素化学討論会
    • Place of Presentation
      仙台市民会館
    • Year and Date
      2016-12-08
    • Related Report
      2016 Research-status Report
  • [Presentation] ホウ素エノラートの求電子的シアノ化反応を利用した高効率β-ケトニトリル合成2016

    • Author(s)
      永田貴也、清川謙介、南方聖司
    • Organizer
      第6回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] ヨウ素酸化剤を活用する第三級炭素のC-H結合酸素官能化2016

    • Author(s)
      伊東 亮、清川謙介、南方聖司
    • Organizer
      第6回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2016-11-14
    • Related Report
      2016 Research-status Report
  • [Presentation] Decarboxylative Ritter-Type Amination Using Iodine Reagents2016

    • Author(s)
      Laura Fra Fernandez, Tomoki Watanabe, Kilian Muniz, Kensuke Kiyokawa, Youhei Takeda, Satoshi Minakata
    • Organizer
      International Symposium on C-O Activation (ISCO-2016)
    • Place of Presentation
      姫路商工会議所
    • Year and Date
      2016-10-25
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Electrophilic Cyanation of Boron Enolates: Efficient Access to β-Ketonitriles2016

    • Author(s)
      Takaya Nagata, Kensuke Kiyokawa, Satoshi Minakata
    • Organizer
      20th International Symposium on Homogeneous Catalysis (ISHCXX)
    • Place of Presentation
      京都テルサ
    • Year and Date
      2016-07-10
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] Ritter-Type Amination of C-H Bonds at Tertiary Carbon Centers Using Iodic Acid as an Oxidant2016

    • Author(s)
      Kensuke Kiyokawa, Kenta Takemoto, Satoshi Minakata
    • Organizer
      5th International Conference on Hypervalent Iodine Chemistry (ICHIC2016)
    • Place of Presentation
      Eurotel Victoria
    • Year and Date
      2016-07-03
    • Related Report
      2016 Research-status Report
    • Int'l Joint Research
  • [Presentation] ヨウ素反応剤を用いた脱炭酸リッター型アミノ化反応2016

    • Author(s)
      渡部友貴、清川謙介、南方聖司
    • Organizer
      第19回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学
    • Related Report
      2016 Research-status Report

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Published: 2016-04-21   Modified: 2019-03-29  

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