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Grignard-type Reaction through the Generation of Oraganometal Reagent from Carboxylates

Research Project

Project/Area Number 24655085
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Synthetic chemistry
Research InstitutionKyushu University

Principal Investigator

KUWANO Ryoichi  九州大学, 理学(系)研究科(研究院), 教授 (20273477)

Project Period (FY) 2012-04-01 – 2014-03-31
Project Status Completed (Fiscal Year 2013)
Budget Amount *help
¥4,160,000 (Direct Cost: ¥3,200,000、Indirect Cost: ¥960,000)
Fiscal Year 2013: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
Fiscal Year 2012: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsニッケル / 求核付加 / 酢酸アリル / アルデヒド / (π-アリル)錯体 / 電子移動 / 有機金属触媒 / 極性転換 / (π-アリル)錯体 / グリニャール反応 / カルボン酸エステル / 低原子価金属還元剤 / 遷移金属触媒
Research Abstract

A mixture of allyl acetate and an aldehyde was heated in an aprotic solvent in the presence of 1,10-phenanthroline-nickel catalyst, zinc powder, and sodium iodide. The resulting mixture gave the desired homoallyl alcohol in good yield. In this transformation, the allyl group of the ester substrate undergoes umpolung to give a nucleophilic species. The resulting species attacks the carbonyl carbon of the aldehyde substrate. The iodide anion may facilitate the electron transfer from zinc powder to the nickel atom.

Report

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

    (3 results)

All 2013 2012

All Presentation (3 results) (of which Invited: 2 results)

  • [Presentation] べンジルエステルを使う触媒反応いろいろ2013

    • Author(s)
      桑野良一
    • Organizer
      科学技術交流財団「ものづくりを革新する新しい触媒研究会:有機分子触媒からクロスカップリングまで」
    • Place of Presentation
      名古屋工業大学
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] パラジウム触媒によるベンジルエステル類の活性化2012

    • Author(s)
      桑野良一
    • Organizer
      第110回触媒討論会
    • Place of Presentation
      九州大学 伊都キャンパス
    • Related Report
      2012 Research-status Report
    • Invited
  • [Presentation] パラジウム触媒によるベンジルエステル類の分子内SN2’型芳香族求核置換反応2012

    • Author(s)
      田中健志
    • Organizer
      第2回CSJ化学フェスタ
    • Place of Presentation
      東京工業大学 大岡山キャンパス
    • Related Report
      2012 Research-status Report

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

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