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Catalytic Addition of be-ta-C-H Bond in Aliphatic Carbonyl Derivatives to Unsaturated Bonds

Research Project

Project/Area Number 16K21441
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeMulti-year Fund
Research Field Synthetic chemistry
Organic chemistry
Research InstitutionTokyo University of Technology

Principal Investigator

UENO Satoshi  東京工科大学, 工学部, 講師 (50514139)

Project Period (FY) 2016-04-01 – 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: ¥910,000 (Direct Cost: ¥700,000、Indirect Cost: ¥210,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywords炭素-炭素結合形成 / 炭素-水素結合官能基化 / カルボニル化合物 / 4-クロモン / 4-キノロン / 結合形成 / パラジウム / ロジウム / 飽和ケトン / β位 / 不飽和結合 / 付加反応 / 触媒 / カルボニル誘導体 / 遷移金属触媒
Outline of Final Research Achievements

The carbon-carbon bond is the fundamental framework of organic molecules, and the development of innovative methods for the C-C bond formation is important. The reaction with 100% atomic efficiency to selectively convert one of many carbon-hydrogen bonds to a carbon-carbon bond is limited to a type of reaction in which a carbon-hydrogen bond is added to an unsaturated bond. In this project, we have found selective addition of the be-ta-C-H bond of the carbonyl compound to obtain the desired product with low yield. Furthermore, in the course of this project, a novel synthetic method of 4-quinolone and 4-chromone was found through a new molecular transformation of be-ta-C-H bond and unsaturated bond.

Academic Significance and Societal Importance of the Research Achievements

有機化合物は、医薬品や農薬、有機材料など多くの場面でわれわれの日常生活に役立っている。しかし現状ではそれらの有機化合物を合成するためには多くの廃棄物が生じる。今回、副生成物を一切生じないいわゆる原子効率100%で有機化合物を合成する方法の開発を行ない、低収率ながら目的生成物を得ることができた。今後引き続き研究を行なっていく。この手法が確立されれば有機合成化学に大きな進歩をもたらし、有機化合物のコスト削減や環境問題の緩和などの社会的な意義をもたらすと考えている。

Report

(4 results)
  • 2018 Annual Research Report   Final Research Report ( PDF )
  • 2017 Research-status Report
  • 2016 Research-status Report
  • Research Products

    (5 results)

All 2019 2017 Other

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

  • [Journal Article] Palladium-catalyzed Benzylic Substitution of Benzyl Carbonates with Phosphorus Nucleophiles2017

    • Author(s)
      Makida Yusuke、Usui Kazumi、Ueno Satoshi、Kuwano Ryoichi
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 12 Pages: 1814-1817

    • DOI

      10.1246/cl.170901

    • NAID

      130006243148

    • Related Report
      2017 Research-status Report
    • Peer Reviewed / Open Access / Int'l Joint Research
  • [Presentation] パラジウム触媒を用いたプロピルケトンとアリル炭酸エステルからの置換ベンゼンの脱水素型合成2019

    • Author(s)
      小池健太、上野 聡
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] o-ヒドロキシプロピオフェノン誘導体のパラジウム触媒脱水素化を利用した4-クロモンの合成2019

    • Author(s)
      竹之下美月、上野 聡
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Presentation] パラジウム触媒による脱水素化を利用したo-フルオロプロピオフェノンと第一級アミンからの4-キノロンの合成2019

    • Author(s)
      赤川友斗、上野 聡
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
  • [Remarks] 東京工科大学工学部応用化学科 上野研究室

    • URL

      https://www.suenotut.com

    • Related Report
      2018 Annual Research Report

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Published: 2016-04-21   Modified: 2020-03-30  

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