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Development of Green Methods for Organic Synthesis Based on New Reaction Systems for Carbon Radical Generation

Research Project

Project/Area Number 24655074
Research Category

Grant-in-Aid for Challenging Exploratory Research

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

Principal Investigator

MIURA Katsukiyo  埼玉大学, 理工学研究科, 教授 (20251035)

Project Period (FY) 2012-04-01 – 2015-03-31
Project Status Completed (Fiscal Year 2014)
Budget Amount *help
¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2013: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2012: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Keywordsラジカル反応 / インジウム触媒 / 有機還元剤 / 炭素ラジカル / 有機ハロゲン化物 / ラジカル還元 / ラジカル環化
Outline of Final Research Achievements

Reactions of carbon radicals are valuable for fine organic synthesis. The reduction of organic halides with metal hydrides and low-valent metals has frequently been used for carbon radical generation. We herein report a new method for carbon radical generation from organic halides using sodium formate, a readily available, less toxic reductant. We found that the indium(III) salt-catalyzed reaction of organic halides with sodium formate in diethylene glycol diethyl ether gave dehalogenated products efficiently. Experimental results suggested that the present reduction should involve a radical mechanism. The radical cyclization of iodoalkynes by this catalytic system also proceeded successfully, and it demonstrated that the present method for carbon radical generation is useful for carbon-carbon bond formation.

Report

(4 results)
  • 2014 Annual Research Report   Final Research Report ( PDF )
  • 2013 Research-status Report
  • 2012 Research-status Report
  • Research Products

    (11 results)

All 2014 2013 Other

All Journal Article (4 results) (of which Peer Reviewed: 4 results) Presentation (1 results) Remarks (6 results)

  • [Journal Article] Regioselective Synthesis of Multisubstituted Benzenes by Palladium-Catalyzed Intermolecular Reaction of β-Iodo-β-silylstyrenes with Alkynes2013

    • Author(s)
      木下英典、高橋博俊、三浦勝清
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 12 Pages: 2962-2965

    • DOI

      10.1021/ol4010883

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Nucleophilic Addition of α-(Dimethylsilyl)nitriles to Aldehydes and Ketones2013

    • Author(s)
      Jinzaki, T.; Arakawa, M.; Kinoshita, H.; Ichikawa, J.; Miura, K.
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 14 Pages: 3750-3753

    • DOI

      10.1021/ol401663u

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Platinum-Catalyzed One-Pot Alkenylation of Aldehydes Using Alkynes and Triethylsilane: Dual Catalysis by Platinum(II) Chloride2013

    • Author(s)
      木下英典、上村亮輔、福田大貴、三浦勝清
    • Journal Title

      Organic Letters

      Volume: 15 Issue: 21 Pages: 5538-5541

    • DOI

      10.1021/ol4026952

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Synthetic Utility of Tribenzyltin Hydride and Its Derivatives as Easily Accessible, Removable, and Decomposable Organotin Reagents2013

    • Author(s)
      三浦勝清
    • Journal Title

      Journal of Organometallic Chemistry

      Volume: 724 Pages: 129-134

    • DOI

      10.1016/j.jorganchem.2012.11.007

    • Related Report
      2012 Research-status Report
    • Peer Reviewed
  • [Presentation] インジウム触媒とギ酸ナトリウムを用いるハロアルカンの還元反応2014

    • Author(s)
      牧野洋平、木下英典、三浦勝清
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋市・名古屋大学
    • Related Report
      2013 Research-status Report
  • [Remarks] 三浦勝清研究室

    • URL

      http://www.apc.saitama-u.ac.jp/ygosei/san_pu_sheng_qing_yan_jiu_shi/top.html

    • Related Report
      2014 Annual Research Report
  • [Remarks] 埼玉大学研究者総覧/三浦勝清

    • URL

      http://s-read.saitama-u.ac.jp/researchers/pages/researcher/BSBxaZoS

    • Related Report
      2014 Annual Research Report
  • [Remarks] 埼玉大学研究機構/研究者たちの素顔Vol19/三浦勝清

    • URL

      http://www.saitama-u.ac.jp/iron/keyaki/keyaki3/report/miura_katsukiyo/

    • Related Report
      2014 Annual Research Report
  • [Remarks] 三浦勝清研究室

    • URL

      http://www.apc.saitama-u.ac.jp/ygosei/san_pu_sheng_qing_yan_jiu_shi/top.html

    • Related Report
      2013 Research-status Report
  • [Remarks] 埼玉大学研究者総覧/三浦勝清

    • URL

      http://s-read.saitama-u.ac.jp/researchers/pages/researcher/BSBxaZoS

    • Related Report
      2013 Research-status Report
  • [Remarks] 三浦勝清研究室

    • URL

      http://www.apc.saitama-u.ac.jp/ygosei/san_pu_sheng_qing_yan_jiu_shi/top.html

    • Related Report
      2012 Research-status Report

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Published: 2013-05-31   Modified: 2019-07-29  

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