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Regioselective Mizoroki-Heck reactions at-position of acrylates

Research Project

Project/Area Number 21550108
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionNara National College of Technology

Principal Investigator

SHIMADA Toyoshi  奈良工業高等専門学校, 物質化学工学科, 教授 (20303802)

Co-Investigator(Kenkyū-buntansha) KAMEI Toshiyuki  奈良工業高等専門学校, 物質化学工学科, 講師 (70534452)
Project Period (FY) 2009 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥4,550,000 (Direct Cost: ¥3,500,000、Indirect Cost: ¥1,050,000)
Fiscal Year 2011: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2010: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
Fiscal Year 2009: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Keywords選択的合成 / 反応 / 溝呂木・ヘック反応 / 位置選択性 / パラジウム触媒 / ホスフィン配位子 / α位
Research Abstract

Mizoroki-Heck reaction is one of the most powerful carboncarbon bondforming reactions. However, Pdcatalyzed Mizoroki-Heck reactions of acrylates with aryl halides give oregioselective products. We examined Pdcatalyzed Mizoroki-Heck reaction in the presence of various bulky ligands, prepared from 1, l' bi2naphthol. Bulkiness of their ligands, however, could not control the sufficient regioselectivity giving aregioselective product. Next, acrylic amides having pyridylmethyl or pyrazolyl group as directing group were prepared, aiming to form more stable palladacycle intermediate leading to aregioselective product. In addition, arylation with enolate intermediate generated during Morita Baylis Hillman reaction was investigated. Unfortunately, these reactions did not afford the desired aregioselective product.

Report

(4 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • 2009 Annual Research Report
  • Research Products

    (2 results)

All 2010

All Presentation (1 results) Book (1 results)

  • [Presentation] 新規4,4'-ジヨードビナフチルジアルデヒドの合成とその誘導化2010

    • Author(s)
      水谷祐介、芝口廣司、亀井稔之、嶋田豊司
    • Organizer
      日本化学会第90春季年会
    • Place of Presentation
      近畿大学
    • Year and Date
      2010-03-27
    • Related Report
      2009 Annual Research Report
  • [Book] 月刊ファインケミカル122010

    • Author(s)
      嶋田豊司
    • Total Pages
      9
    • Publisher
      シーエムシー出版
    • Related Report
      2010 Annual Research Report

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Published: 2009-04-01   Modified: 2016-04-21  

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