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Development of a new strategy toward selective cleavage of unactivated sp3C-H bonds and its application to bond forming reactions

Research Project

Project/Area Number 26620087
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

Kambe Nobuaki  大阪大学, 工学(系)研究科(研究院), 教授 (60144432)

Project Period (FY) 2014-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥3,900,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥900,000)
Fiscal Year 2015: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2014: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Keywords炭素―水素結合切断 / 炭素―水素結合官能基化 / カルコゲン / 触媒 / 含窒素複素環
Outline of Final Research Achievements

In this study, we developed transition metal-catalyzed sulfenylation, selenylation, and sulfonylation of arenes and heteroarenes through sp2C-H bond cleavage. In addition, we also found that Cu catalyzes intramolecular amination of unactivated sp3C-H bond to give indoline derivatives.
In order to develop a new methodology of C-H bond cleavage without the aid of directing group in substrates, we designed a new rhodium catalyst bearing cyclodextrin moiety, which could capture the substrate in its hydrophobic cavity through supramolecular complexation to facilitate C-H bond cleavage.

Report

(3 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Research-status Report
  • Research Products

    (14 results)

All 2015 2014 Other

All Int'l Joint Research (1 results) Journal Article (5 results) (of which Int'l Joint Research: 1 results,  Peer Reviewed: 5 results,  Acknowledgement Compliant: 2 results) Presentation (8 results) (of which Int'l Joint Research: 2 results,  Invited: 1 results)

  • [Int'l Joint Research] 湖南大学(中国)

    • Related Report
      2015 Annual Research Report
  • [Journal Article] Copper-mediated thiolation of carbazole derivatives and related N-heterocycle compounds2015

    • Author(s)
      Longzhi Zhu, Xin Cao, Renhua Qiu, Takanori Iwasaki, Vutukuri Prakash Reddy, Xinhua Xu, Shuang-Feng Yin, and Nobuaki Kambe
    • Journal Title

      RSC Adv.

      Volume: 5 Issue: 49 Pages: 39358-39365

    • DOI

      10.1039/c5ra04965b

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Int'l Joint Research
  • [Journal Article] Nickel-catalyzed synthesis of diarylsulfides and sulfones via C-H bond functionalization of arylamides2015

    • Author(s)
      Vutukuri Prakash Reddy, Renhua Qiu, Takanori Iwasaki, and Nobuaki Kambe
    • Journal Title

      Org. Biomol. Chem.

      Volume: 13 Issue: 24 Pages: 6803-6813

    • DOI

      10.1039/c5ob00149h

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] (1)The Palladium-Catalyzed Intermolecular C-H Chalcogenation of Arenes2015

    • Author(s)
      Renhua Qiu, Vutukuri Prakash Reddy, Takanori Iwasaki, Nobuaki Kambe
    • Journal Title

      J. Org. Chem.

      Volume: 80 (1) Issue: 1 Pages: 367-374

    • DOI

      10.1021/jo502402d

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Palladium-Catalyzed Insertion Reactions of Isocyanides into Thiocarbamates and Selenocarbamates2015

    • Author(s)
      Daisuke Shiro, Shin-ichi Fujiwara, Susumu Tsuda, Takanori Iwasaki, Hitoshi Kuniyasu, Nobuaki Kambe
    • Journal Title

      Chem. Lett.

      Volume: 40 Issue: 4 Pages: 465-467

    • DOI

      10.1246/cl.141141

    • NAID

      130005062143

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Decarbonylative Rearrangement of N-Allenyl Seleno- and Tellurocarbamates2014

    • Author(s)
      Daisuke Shiro, Hiroyuki Nagai, Shin-ichi Fujiwara, Susumu Tsuda, Takanori Iwasaki, Hitoshi Kuniyasu, Nobuaki Kambe
    • Journal Title

      Heteroatom Chem.

      Volume: 25 Issue: 6 Pages: 518-524

    • DOI

      10.1002/hc.21217

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Presentation] “Synthesis of cyclopentadienyl rhodium complexes bearing a cyclodextrin and their application to catalytic reactions”2015

    • Author(s)
      Hiroki Yamauchi, Susumu Tsuda, Takanori Iwasaki, Shin-ichi Fujiwara, Hitoshi Kuniyasu, Nobuaki Kambe
    • Organizer
      The International Chemical Congress of Pacific Basin Societies 2015 (PACIFICHEM 2015)
    • Place of Presentation
      Honolulu
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] “Carbon-Carbon Bond Forming Reactions Catalyzed by Transition Metal Ate Complexes”2015

    • Author(s)
      Nobuaki Kambe
    • Organizer
      The 7th Spanish Portuguese Japanese Organic Chemistry Symposium (7th SPJ-OCS)
    • Place of Presentation
      Seville (Spain)
    • Year and Date
      2015-06-03
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] メチル化シクロデキストリンを連結したシクロペンタジエニル配位子の合成と応用2015

    • Author(s)
      山内 大樹、津田 進、岩﨑孝紀、藤原眞一、国安 均、神戸 宣明
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      千葉県(日本大学船橋キャンパス)
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Syntheses and Reactions of Organochalcogen Compounds Catalyzed by Transition Metals2014

    • Author(s)
      Nobuaki Kambe,
    • Organizer
      IXXth International Symposium on Selected Problems of Chemistry of Acyclic and Cyclic Heteroorganic Compounds
    • Place of Presentation
      the CMMS PAS in Lodz (Poland)
    • Year and Date
      2014-11-21
    • Related Report
      2014 Research-status Report
  • [Presentation] メチル化シクロデキストリンに連結したNHC配位子を用いるロジウム触媒によるアルデヒドの不斉アリール化反応2014

    • Author(s)
      山内大樹、津田 進、岩﨑孝紀、藤原眞一、国安 均、神戸宣明
    • Organizer
      第4回CSJ化学フェスタ2014 ―日本化学会秋季事業―
    • Place of Presentation
      東京(タワーホール船堀)
    • Year and Date
      2014-10-14 – 2014-10-16
    • Related Report
      2014 Research-status Report
  • [Presentation] メチル化CD連結NHC-Rh触媒によるアリールボロン酸のエナンチオ選択的1,2-付加反応2014

    • Author(s)
      山内大樹、津田 進、岩﨑孝紀、藤原眞一、国安 均、神戸宣明
    • Organizer
      第31回シクロデキストリンシンポジウム
    • Place of Presentation
      島根(島根県民会館)
    • Year and Date
      2014-09-11 – 2014-09-12
    • Related Report
      2014 Research-status Report
  • [Presentation] メチル化シクロデキストリンに連結したNHC配位子を用いるロジウム触媒によるアルデヒドの不斉アリール化反応2014

    • Author(s)
      山内大樹、津田 進、岩﨑孝紀、藤原眞一、国安 均、神戸宣明
    • Organizer
      第47回有機金属若手の会 夏の学校
    • Place of Presentation
      広島(大久野島休暇村)
    • Year and Date
      2014-09-01 – 2014-09-03
    • Related Report
      2014 Research-status Report
  • [Presentation] arbon-Carbon Bond Forming Reactions Catalyzed by Rhodium Complexes2014

    • Author(s)
      Nobuaki Kambe
    • Organizer
      The XXVI International Conference on Organometallic Chemistry (ICOMC 2014)
    • Place of Presentation
      札幌
    • Year and Date
      2014-07-15
    • Related Report
      2014 Research-status Report
    • Invited

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Published: 2014-04-04   Modified: 2022-01-31  

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