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Copper-catalyzed C(sp3)-H functionalization for the synthesis of various heterocyclic compounds

Research Project

Project/Area Number 17K15418
Research Category

Grant-in-Aid for Young Scientists (B)

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

Principal Investigator

Nozawa-Kumada Kanako  東北大学, 薬学研究科, 助教 (30748504)

Project Period (FY) 2017-04-01 – 2019-03-31
Project Status Completed (Fiscal Year 2018)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2018: ¥2,470,000 (Direct Cost: ¥1,900,000、Indirect Cost: ¥570,000)
Fiscal Year 2017: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywords炭素-水素結合官能基化 / 複素環化合物 / 銅触媒 / 酸化反応 / イソインドリノン / ラクトン / 触媒・化学プロセス / 炭素ー水素結合官能基化 / β-ラクタム / 有機化学 / C-H官能基化 / 遷移金属
Outline of Final Research Achievements

Direct functionalization of C-H bonds is a highly attractive method because it does not require any pre-functionalized starting materials. Therefore, this method can attain the atom- and step-economic synthesis of organic compounds. We have developed copper-catalyzed C(sp3)-H functionalization of 2-alkyl-N-arylbenzamides for the synthesis of N-aryl-isoindolinones. In this study, this method was applied to the synthesis of bioactive compounds, indoprofen and DWP205190. Furthermore, we developed a novel C(sp3)-H bond lactonization of 2-alkylbenzoic acids using peroxydisulfate as the sole oxidant.

Academic Significance and Societal Importance of the Research Achievements

C(sp3)-H結合の官能基化により,含sp3炭素複素環化合物であるイソインドリノンやラクトンの実用的な合成法を確立することができた.本手法は今後様々な複素環骨格構築法に応用していくことができると考えている.また,本研究成果により,直截的に生理活性物質や機能性材料の基本骨格として多く存在する含 sp3 炭素複素環化合物を安価かつ効率的に合成することが可能になると考えられ,医学・薬学・材料科学等の広範な分野に大きく貢献できる.

Report

(3 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • Research Products

    (26 results)

All 2019 2018 2017 Other

All Journal Article (8 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 8 results) Presentation (17 results) (of which Int'l Joint Research: 1 results,  Invited: 3 results) Remarks (1 results)

  • [Journal Article] Direct Carboxylation of Electron‐Rich Heteroarenes Promoted by LiO‐tBu with CsF and [18]Crown‐62019

    • Author(s)
      Shigeno Masanori、Hanasaka Kazuya、Sasaki Keita、Nozawa‐Kumada Kanako、Kondo Yoshinori
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 13 Pages: 3235-3239

    • DOI

      10.1002/chem.201805926

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Phosphazene base t-Bu-P4-catalyzed methoxy-alkoxy exchange reaction on (hetero)arenes2019

    • Author(s)
      Shigeno Masanori、Hayashi Kazutoshi、Nozawa-Kumada Kanako、Kondo Yoshinori
    • Journal Title

      Chemistry - A European Journal

      Volume: 25 Issue: 24 Pages: 6077-6081

    • DOI

      10.1002/chem.201900498

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Amide-Base System of TMAF and N(TMS)3 for Deprotonative Coupling of Benzylic C(sp3)-H Bonds with Carbonyls2019

    • Author(s)
      Shigeno Masanori、Nakaji Kunihito、Nozawa-Kumada Kanako、Kondo Yoshinori
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 8 Pages: 2588-2592

    • DOI

      10.1021/acs.orglett.9b00550

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Generation and Characterization of Anti-phenyl Sulfate Monoclonal Antibodies and a Potential Use for Phenyl Sulfate Analysis in Human Blood2018

    • Author(s)
      Kanemitsu Yoshitomi、Tsukamoto Hiroki、Matsumoto Yotaro、Nozawa-Kumada Kanako、Kondo Yoshinori、Abe Takaaki、Tomioka Yoshihisa
    • Journal Title

      Biological and Pharmaceutical Bulletin

      Volume: 41 Issue: 8 Pages: 1170-1177

    • DOI

      10.1248/bpb.b17-00925

    • NAID

      130007429804

    • ISSN
      0918-6158, 1347-5215
    • Year and Date
      2018-08-01
    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Construction of Biaryl Scaffolds from Iodoarenes and C-H Heteroarenes Using an Amide Base Generated in situ from Aminosilane and Fluoride Anion2018

    • Author(s)
      Shigeno Masanori、Kai Yusuke、Yamada Tetsuya、Hayashi Kazutoshi、Nozawa-Kumada Kanako、Denneval Charline、Kondo Yoshinori
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 7 Issue: 10 Pages: 2082-2086

    • DOI

      10.1002/ajoc.201800438

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Catalytic Deprotonative α-Formylation of Heteroarenes by an Amide Base Generated in Situ from Tetramethylammonium Fluoride and Tris(trimethylsilyl)amine2018

    • Author(s)
      Shigeno Masanori、Fujii Yuki、Kajima Akihisa、Nozawa-Kumada Kanako、Kondo Yoshinori
    • Journal Title

      Organic Process Research & Development

      Volume: 23 Issue: 4 Pages: 443-451

    • DOI

      10.1021/acs.oprd.8b00247

    • Related Report
      2018 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Super electron donor-mediated reductive transformation of nitrobenzenes: a novel strategy to synthesize azobenzenes and phenazines2018

    • Author(s)
      Nozawa-Kumada Kanako、Abe Erina、Ito Shungo、Shigeno Masanori、Kondo Yoshinori
    • Journal Title

      Organic & Biomolecular Chemistry

      Volume: 印刷中 Issue: 17 Pages: 3095-3098

    • DOI

      10.1039/c8ob00271a

    • Related Report
      2017 Research-status Report
    • Peer Reviewed
  • [Journal Article] Deprotonative Silylation of Aromatic C-H Bonds Mediated by a Combination of Trifluoromethyltrialkylsilane and Fluoride2017

    • Author(s)
      Nozawa-Kumada Kanako、Osawa Sayuri、Sasaki Midori、Chataigner Isabelle、Shigeno Masanori、Kondo Yoshinori
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 18 Pages: 9487-9496

    • DOI

      10.1021/acs.joc.7b01525

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Int'l Joint Research
  • [Presentation] シリルラクトン化反応によるフタリド合成法の開発2019

    • Author(s)
      小島匠人,熊田佳菜子,根東義則
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] HSiEt3/I2によるアルキンのZ-選択的還元反応の開発2019

    • Author(s)
      野口 小都,熊田 佳菜子,根東 義則
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 分子状酸素を用いた銅触媒によるベンジル位C(sp3)-H結合酸素官能基化反応の開発2019

    • Author(s)
      松澤雄太,熊田佳菜子,根東義則
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 分子状酸素を用いた銅触媒C(sp3)-H結合官能基化によるラクトン合成法の開発2019

    • Author(s)
      熊田佳菜子,黒須智,根東義則
    • Organizer
      日本薬学会第139年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 銅触媒を用いた酸化的C-H結合官能基化による含sp3炭素複素環化合物の効率的合成法の開発2018

    • Author(s)
      熊田佳菜子,佐賀怜,黒須智,亀山雄大,門川純,根東義則
    • Organizer
      第16回次世代を担う有機化学シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 酸化的 C(sp3)-H 結合官能基化によるフタリド骨格構築法の開発2018

    • Author(s)
      熊田佳菜子,黒須智,根東義則
    • Organizer
      第29回万有仙台シンポジウム
    • Related Report
      2018 Annual Research Report
  • [Presentation] 有機超電子供与剤を用いたニトロベンゼン類及びジチアン類の新規還元反応の開発2018

    • Author(s)
      熊田佳菜子,安部瑛里奈,伊藤峻吾,野口小都,根東義則
    • Organizer
      第48回複素環化学討論会
    • Related Report
      2018 Annual Research Report
  • [Presentation] 分子状酸素を酸化剤として用いた銅触媒 C(sp3)-H 結合官能基化によるラクトン合成法の開発2018

    • Author(s)
      熊田佳菜子,黒須智,根東義則
    • Organizer
      第35回有機合成化学セミナー
    • Related Report
      2018 Annual Research Report
  • [Presentation] 遷移金属触媒および系内発生塩基を利用した炭素―水素結合官能基化反応の開発2018

    • Author(s)
      熊田佳菜子
    • Organizer
      第40回東北薬学セミナー
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Copper-Catalyzed Oxidative C(sp3)-H Functionalization for the Synthesis of Heteroaromatics2018

    • Author(s)
      Kanako Nozawa-Kumada, Satoshi Saga, Satoshi Kurosu, Takehiro Kameyama, Jun Kadokawa, Yoshinori Kondo
    • Organizer
      International Symposium on Pure & Applied Chemistry Langkawi 2018
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Copper-catalyzed intramolecular oxidative C(sp3)-H functionalization for the synthesis of heteroaromatics2018

    • Author(s)
      Kumada, K.; Saga, S.; Kurosu, S.; Kondo, Y.
    • Organizer
      255th ACS National Meeting
    • Related Report
      2017 Research-status Report
    • Int'l Joint Research
  • [Presentation] ペルオキソ二硫酸塩を用いた酸化的C(sp3)-H結合官能基化によるラクトン類合成法の開発2018

    • Author(s)
      黒須智,熊田佳菜子,根東義則
    • Organizer
      日本薬学会第138回年会
    • Related Report
      2017 Research-status Report
  • [Presentation] 銅触媒を用いたC-H 結合官能基化を経由する含sp3炭素複素環化合物の効率的合成法2017

    • Author(s)
      熊田佳菜子,佐賀怜,亀山雄大,門川純,根東義則
    • Organizer
      第6回JACI/GSCシンポジウム
    • Related Report
      2017 Research-status Report
  • [Presentation] Copper-catalyzed Intramolecular C(sp3)-H Functionalization for the Synthesis of Heteroaromatics2017

    • Author(s)
      Kumada, K.; Saga, S.; Kurosu, S.; Kameyama, T.; Kadokawa, J.; Kondo, Y.
    • Organizer
      第64回 有機金属化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 銅触媒による C(sp3)-H 結合官能基化を経由したβ-ラクタム環構築法の開発2017

    • Author(s)
      佐賀怜,熊田佳菜子,重野真徳,根東義則
    • Organizer
      第47回 複素環化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 銅触媒を用いた酸化的C-H結合官能基化による含sp3炭素複素環化合物の効率的合成法2017

    • Author(s)
      熊田佳菜子,佐賀怜,黒須智,亀山雄大,門川純,重野真徳,根東義則
    • Organizer
      第47回 複素環化学討論会
    • Related Report
      2017 Research-status Report
  • [Presentation] 遷移金属触媒および有機分子触媒を利用した炭素-水素結合官能基化反応2017

    • Author(s)
      熊田 佳菜子
    • Organizer
      日本薬学会東北支部 第16回化学系若手研究者セミナー
    • Related Report
      2017 Research-status Report
    • Invited
  • [Remarks] 分子変換化学分野

    • URL

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

    • Related Report
      2017 Research-status Report

URL: 

Published: 2017-04-28   Modified: 2020-03-30  

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