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Synthetic Organic Chemistry with a New Concept of Microwave Chemistry

Research Project

Project/Area Number 17H03061
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKeio University

Principal Investigator

YAMADA TOHRU  慶應義塾大学, 理工学部(矢上), 教授 (40296752)

Project Period (FY) 2017-04-01 – 2020-03-31
Project Status Completed (Fiscal Year 2019)
Budget Amount *help
¥18,200,000 (Direct Cost: ¥14,000,000、Indirect Cost: ¥4,200,000)
Fiscal Year 2019: ¥3,510,000 (Direct Cost: ¥2,700,000、Indirect Cost: ¥810,000)
Fiscal Year 2018: ¥5,330,000 (Direct Cost: ¥4,100,000、Indirect Cost: ¥1,230,000)
Fiscal Year 2017: ¥9,360,000 (Direct Cost: ¥7,200,000、Indirect Cost: ¥2,160,000)
Keywordsマイクロ波 / 選択的合成 / 不斉合成 / ナザロフ環化反応
Outline of Final Research Achievements

The microwave specific effect was verified in the Nazarov cyclization reaction. Based on the quantification of the reaction acceleration by kinetic analysis, the maximum acceleration of 5.8 times was confirmed. Reaction acceleration was also observed in the thermal Nazarov cyclization reaction without any loss of chiral transfer rate. In the development research of absolute asymmetric synthesis using circularly polarized microwaves, a joint research was made on the setting of reaction system by physical measurement of circularly polarized microwaves. Furthermore, we have developed a joint research on the hypothesis that the microwave specificity effect is based on entropy effect, and found a possibility to elucidate the mechanism by terahertz spectroscopy.

Academic Significance and Societal Importance of the Research Achievements

マイクロ波加熱は日常にも利用され,技術としては成熟しているが,加熱メカニズムも完全には理解されていない。合成有機化学的にもマイクロ波特異効果はいまだに懐疑的な意見も多い。本研究では,マイクロ波効果の実験的検証に基づくマイクロ波利用の普及を目指し,定量的な取扱いによるマイクロ波効果のメカニズムの解明に迫った。

Report

(4 results)
  • 2019 Annual Research Report   Final Research Report ( PDF )
  • 2018 Annual Research Report
  • 2017 Annual Research Report
  • Research Products

    (24 results)

All 2020 2019 2018 2017

All Journal Article (9 results) (of which Peer Reviewed: 8 results) Presentation (13 results) (of which Int'l Joint Research: 6 results,  Invited: 11 results) Book (2 results)

  • [Journal Article] Thermal Decarboxylative Nazarov Cyclization of Cyclic Enol Carbonates Involving Chirality Transfer2020

    • Author(s)
      Kozuma Akane、Komatsuki Keiichi、Saito Kodai、Yamada Tohru
    • Journal Title

      Chemistry Letters

      Volume: 49 Issue: 1 Pages: 60-63

    • DOI

      10.1246/cl.190763

    • NAID

      130007782551

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] マイクロ波有機合成化学の ルネサンス 特異効果はあるのか!2020

    • Author(s)
      山田 徹
    • Journal Title

      化学と工業

      Volume: 72(3) Pages: 234-235

    • Related Report
      2019 Annual Research Report
  • [Journal Article] Kolbe-Schmitt type reaction under ambient conditions mediated by an organic base2019

    • Author(s)
      Sadamitsu Yuta、Okumura Akira、Saito Kodai、Yamada Tohru
    • Journal Title

      Chemical Communications

      Volume: 55 Issue: 66 Pages: 9837-9840

    • DOI

      10.1039/c9cc04550c

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Decarboxylative Nazarov Cyclization-Based Chirality Transfer for Asymmetric Synthesis of 2-Cyclopentenones2019

    • Author(s)
      Komatsuki Keiichi、Kozuma Akane、Saito Kodai、Yamada Tohru
    • Journal Title

      Organic Letters

      Volume: 21 Issue: 17 Pages: 6628-6632

    • DOI

      10.1021/acs.orglett.9b02107

    • Related Report
      2019 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Microwave-specific Effect on Enantioselective Reactions2018

    • Author(s)
      Sawada Taichi、Yamada Tohru
    • Journal Title

      Journal of the Japan Petroleum Institute

      Volume: 61 Issue: 2 Pages: 121-128

    • DOI

      10.1627/jpi.61.121

    • NAID

      130006415543

    • ISSN
      1346-8804, 1349-273X
    • Year and Date
      2018-03-01
    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Amidation Reaction of Carboxylic Acid with Formamide Derivative Using SO3・pyridine2018

    • Author(s)
      Kawano Shota、Saito Kodai、Yamada Tohru
    • Journal Title

      Chemistry Letters

      Volume: 47 Issue: 4 Pages: 584-586

    • DOI

      10.1246/cl.171216

    • NAID

      130006638920

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Access to Tetronic Acids via Silver-Catalyzed CO2 Incorporation into Conjugated Ynones2017

    • Author(s)
      Sadamitsu Yuta、Komatsuki Keiichi、Saito Kodai、Yamada Tohru
    • Journal Title

      Organic Letters

      Volume: 19 Issue: 12 Pages: 3191-3194

    • DOI

      10.1021/acs.orglett.7b01309

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Silver-catalyzed Three-component Reaction of Propargylic Amines, Carbon Dioxide, and N-Bromosuccinimide for Stereoselective Preparation of (E)-Bromovinyloxazolidinones2017

    • Author(s)
      Sugiyama Nao、Ohseki Masatoshi、Kobayashi Ryo、Sekine Kohei、Saito Kodai、Yamada Tohru
    • Journal Title

      Chemistry Letters

      Volume: 46 Issue: 9 Pages: 1323-1326

    • DOI

      10.1246/cl.170541

    • NAID

      130006067864

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Stereospecific Decarboxylative Nazarov Cyclization Mediated by Carbon Dioxide for the Preparation of Highly Substituted 2-Cyclopentenones2017

    • Author(s)
      Komatsuki Keiichi、Sadamitsu Yuta、Sekine Kohei、Saito Kodai、Yamada Tohru
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 56 Issue: 38 Pages: 11594-11598

    • DOI

      10.1002/anie.201705909

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Presentation] 銀触媒を用いる二酸化炭素の固定反応2019

    • Author(s)
      山田 徹
    • Organizer
      ファインケミカルズ研究会第105回例会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] マイクロ波熱的効果と特異効果の分離:不斉触媒反応の場合2019

    • Author(s)
      山田 徹
    • Organizer
      第13回日本電磁波エネルギー応用学会シンポジウム
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] CO2 Incorporation Reactions and CO2 Mediated Reactions2019

    • Author(s)
      山田 徹
    • Organizer
      第20回有機合成指向有機金属化学国際会議(OMCOS20)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] マイクロ波特異効果と合成有機化学反応2019

    • Author(s)
      山田 徹
    • Organizer
      北海道大学フロンティア化学教育研究センター講演会
    • Related Report
      2019 Annual Research Report
    • Invited
  • [Presentation] CO2 Incorporation Reactions and CO2 Mediated Reactions2019

    • Author(s)
      山田 徹
    • Organizer
      第1回全国二酸化炭素資源化利用学術会議(@南開大学)
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Microwave Effect on Organic Reactions2019

    • Author(s)
      山田 徹
    • Organizer
      18th Asian Chemical Congress
    • Related Report
      2019 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Silver-Catalyzed C-C Bond Formation with Carbon Dioxide2019

    • Author(s)
      T. Yamada
    • Organizer
      China-Japan Joint Symposium on Catalysis for Transformation of Carbon Dioxide
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] マイクロ波の加熱効果と特異効果:有機合成反応への適用2019

    • Author(s)
      山田徹
    • Organizer
      日本化学会第99春季年会
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] マイクロ波効果の新たな可能性2018

    • Author(s)
      山田徹
    • Organizer
      2018 Microwave Conference
    • Related Report
      2018 Annual Research Report
    • Invited
  • [Presentation] Microwave Effect on Enantioselective Catalysis2018

    • Author(s)
      T. Yamada
    • Organizer
      The 13th International Symposium on Organic Reaction
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] Microwave Specific Effect on Catalytic Enantioselective Reactions2018

    • Author(s)
      T. Yamada
    • Organizer
      International Symposium on Catalysis and Fine Chemicals 2018
    • Related Report
      2018 Annual Research Report
    • Int'l Joint Research / Invited
  • [Presentation] 有機塩基を用いるレゾルシノール類に対するKolbe-Schmitt反応2018

    • Author(s)
      定光勇太・奥村晶・齊藤巧泰・山田徹
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 脱炭酸型ナザロフ環化を介した不斉転写反応による光学活性2-シクロペンテノンの合成2018

    • Author(s)
      駒月恵一・上妻紅音・齊藤巧泰・山田徹
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Book] Silver Catalysis in Organic Synthesis2019

    • Author(s)
      T. Yamada, K. Sekine, Y, Sadamitsu, K. Saito
    • Total Pages
      32
    • Publisher
      Wiley-VCH
    • ISBN
      9783527342815
    • Related Report
      2018 Annual Research Report
  • [Book] マイクロ波加熱の基礎と産業応用2017

    • Author(s)
      山田 徹
    • Total Pages
      13
    • Publisher
      R&D支援センター
    • ISBN
      9784905507154
    • Related Report
      2017 Annual Research Report

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Published: 2017-04-28   Modified: 2021-02-19  

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