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レドックス活性化に基づく不活性炭素化合物の高効率分子変換

Research Project

Project/Area Number 19020061
Research Category

Grant-in-Aid for Scientific Research on Priority Areas

Allocation TypeSingle-year Grants
Review Section Science and Engineering
Research InstitutionOsaka Prefecture University

Principal Investigator

小川 昭弥  Osaka Prefecture University, 工学研究科, 教授 (30183031)

Co-Investigator(Kenkyū-buntansha) 野元 昭弘  大阪市立大学, 工学研究科, 助教 (60405347)
Project Period (FY) 2007 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥3,800,000 (Direct Cost: ¥3,800,000)
Fiscal Year 2008: ¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2007: ¥1,900,000 (Direct Cost: ¥1,900,000)
Keywordsレドックス活性化 / バナジウム錯体触媒 / 環境低負荷 / 酸素酸化 / 不活性炭素化合物 / 光活性化 / C-F結合活性化 / 二酸化炭素活性化
Research Abstract

本研究では、炭素原子を含む不活性結合をレドックスアクティブな遷移金属錯体触媒で活性化することにより、高選択的な酸化的分子変換や還元的分子変換を明らかにし、さらにこれらの反応を基軸とする各種ヘテロ官能基の高効率・高選択的調製法を開発することを目的としている。
本年度は、遷移金属触媒系や光照射系を応用した新反応の開発を行い、これらの新反応群による原子効率の良いヘテロ官能基導入反応について明らかにした。すなわち、(1)バナジウム錯体触媒による炭素一窒素単結合の常圧酸素酸化を検討し、アミンからイミンの高選択的合成に成功した。(2)広範囲の低原子価希土類による炭素-ハロゲン単結合の還元的分子変換を検討し、これに基づいて、光照射下での希土類金属による共役ジエンのアシル化反応に成功した。さらに、本希土類複合試薬はケイ素-ハロゲン結合の還元にも有効であり、ポリシラン合成にも適用可能であることが明らかとなった。(3)リンや硫黄、セレンなどのヘテロ原子間単結合を遷移金属触媒や光照射により活性化することにより、炭素-炭素不飽和結合への各種ヘテロ官能基の高選択的導入法を明らかにした。
以上の述べてきたように、本研究では酸化・還元やヘテロ官能基導入の新手法を開拓することにより、種々の炭素資源に炭素-ヘテロ原子単結合(C-S、C-Se、C-P、C-Si)や炭素-ヘテロ原子多重結合(C=0、C=N)を高選択的に導入できる原子効率の高い反応群を明らかにした。

Report

(2 results)
  • 2008 Annual Research Report
  • 2007 Annual Research Report
  • Research Products

    (36 results)

All 2009 2008 2007 Other

All Journal Article (10 results) (of which Peer Reviewed: 10 results) Presentation (16 results) Book (4 results) Remarks (4 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] On the potentially excellent reducing ability of a series of low-valent rare earths induced by photoirradiation2009

    • Author(s)
      Tomisaka, Y. ; Nomoto, A. ; Ogawa A.
    • Journal Title

      Tetrahedron Letters 50

      Pages: 584-586

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoaccelerated Reductive Coupling of Acid Chlorides with Conjugate Dienes and Styrenes by Use of Neodymium Metal in N, N-Dimethylacetamide2009

    • Author(s)
      Li, Z. f. ; Tomisaka, Y. ; Nomoto, A. ; Zhang, Y. ; Ogawa A.
    • Journal Title

      Chemistry Letters 38

      Pages: 16-17

    • NAID

      10023990066

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Highly Regioselective Palladium-Catalyzed Hydrophosphination of Alkynes Using a Diphosphine-Hydrosilane Binary System2008

    • Author(s)
      Kawaguchi, S. ; Nagata, S. ; Nomoto, A. ; Sonoda, M. ; Ogawa A., 他3名
    • Journal Title

      Journal of Organic Chemistry 73

      Pages: 7928-7933

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper(0)-induced aminocyclopropanation of olefins via deselenation of N, N-disubstituted aromatic selenoamides2008

    • Author(s)
      Mitamura T., Ogawa A., 他2名
    • Journal Title

      Tetrahedron 64

      Pages: 9983-9988

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoinduced highly selective thiophosphination of alkynes using a (PhS)_2/(Ph_2P)_2 binary system2008

    • Author(s)
      Shirai T., Ogawa A. 他2名
    • Journal Title

      Tetrahedron Letters 49

      Pages: 4043-4046

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Novel photoinduced reduction of conjugate dienes by the combination of benzenethiol and diphenyl diselentide2007

    • Author(s)
      Mitamura T., Ogawa A. 他3名
    • Journal Title

      Bulletin of the Chemical Society of Japan 80

      Pages: 1444-1446

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Lewis acid-catalyzed reduction of dithioacetals by 1,4-cyclohexadiene2007

    • Author(s)
      Ikeshita K., Ogawa A. 他2名
    • Journal Title

      Tetrahedron Letters 48

      Pages: 3025-3028

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Photoinduced thiotelluration of isocyanides by using a (PhS)(2)-(PhTe)(2) mixed system,and its application to bisthiolation via radical cyclization2007

    • Author(s)
      Mitamura T., Ogawa A. 他5名
    • Journal Title

      Tetrahedron Letters 48

      Pages: 5953-5957

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A highly regioselective hydrophosphination of terminal alkynes with tetraphenyldiphosphine in the presence of palladium catalyst2007

    • Author(s)
      Nagata S., Ogawa A. 他5名
    • Journal Title

      Tetrahedron Letters 48

      Pages: 6637-6640

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A novel palladium(0)-catalyzed addition of diphenyl disulfide to allenes leading to vicinal disulfides and its application to carbonylation with carbon monoxide2007

    • Author(s)
      Kodama S., Ogawa A. 他5名
    • Journal Title

      Tetrahedron Letters 48

      Pages: 6312-6317

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] トリフェニルボスフィン存在下ジスルフィドと水を用いたアレン類の触媒的ヒドロチオレーション2009

    • Author(s)
      小玉晋太朗, 小川昭弥
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      東京
    • Year and Date
      2009-03-30
    • Related Report
      2008 Annual Research Report
  • [Presentation] アミン類の高選択的な常圧酸素酸化を指向したバナジウム触媒系の構築2009

    • Author(s)
      吉田潤, 小玉晋太朗, 野元昭宏, 植嶌陸男, 小川昭弥
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      東京
    • Year and Date
      2009-03-30
    • Related Report
      2008 Annual Research Report
  • [Presentation] 空孔内に亜鉛金属を有するヘミクリプトファンの合成と性質2009

    • Author(s)
      牧田佳真, 小川昭弥, 他3名
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      東京
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] カルコゲン元素を導入したジビニルベンゼン誘導体の配位挙動2009

    • Author(s)
      湊辺悠太, 野元昭宏, 小川昭弥
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      東京
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] アルケンおよびアルキン共存下、粉末銅に誘起されるセレノアミドの脱セレノ化反応2009

    • Author(s)
      三田村健範, 小川昭弥
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      東京
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] 可視光照射下、ジフェニルジテルリドによるo-エチニルイソシアニドの分子内ラジカル環化反応2009

    • Author(s)
      岩田起皆代, 三田村健範, 小川昭弥
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      東京
    • Year and Date
      2009-03-28
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒存在下、ジホスフィン-ヒドロシラン複合系を用いたビニルボスフィン類の合成2008

    • Author(s)
      川口真一, 小川昭弥, 他3名
    • Organizer
      第35回有機典型元素化学討論会
    • Place of Presentation
      東京
    • Year and Date
      2008-12-13
    • Related Report
      2008 Annual Research Report
  • [Presentation] パラジウム触媒存在下エチニル基を有するポルフィリンへのカルコゲン部位の位置選択的な導入2008

    • Author(s)
      椎野豪, 野元昭宏, 小川昭弥
    • Organizer
      第55回有機金属化学討論会
    • Place of Presentation
      大阪
    • Year and Date
      2008-09-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] Photoinduced Intramolecular Cyclization of Isocyanides Bearing an Unsaturated Bond by Using (PhS)_2-(PhTe)_2 Mixed System2008

    • Author(s)
      T. Mitamura, A. Nomoto, A. Ogaiva
    • Organizer
      10th International Symposium on Organic Free Radicals (ISOFR 10) and 3rd Pacific Symposium on Radical Chemistry (PSRC 3)
    • Place of Presentation
      Australia, Gladstone
    • Year and Date
      2008-08-06
    • Related Report
      2008 Annual Research Report
  • [Presentation] Highly Selective Introduction of Heteroatom Groups into Unsaturated Bonds by Using Heteroatom-Mixed System2008

    • Author(s)
      A. Nomoto, A. Ogawa
    • Organizer
      10th International Symposium on Organic Free Radicals (ISOFR 10) and 3rd Pacific Symposium on Radical Chemistry (PSRC 3)
    • Place of Presentation
      Australia, Gladstone
    • Year and Date
      2008-08-04
    • Related Report
      2008 Annual Research Report
  • [Presentation] Development of Oxidation of Alcohols with Molecular Oxygen Catalyzed by Oxovanadium Complexes2008

    • Author(s)
      S. Kodama, A. Ogawa, 他2名
    • Organizer
      10th International Symposium on Organic Free Radicals (ISOFR 10) and 3rd Pacific Symposium on Radical Chemistry (PSRC 3)
    • Place of Presentation
      Australia, Gladstone
    • Year and Date
      2008-08-04
    • Related Report
      2008 Annual Research Report
  • [Presentation] Development of the Highly Selective Oxidation of Alcohols with Oxygen Catalyzed by Oxovanadium Complexes2008

    • Author(s)
      S. Kodama, A. Ogawa
    • Organizer
      Third International Conference on Advanced Organic Synthesis Directed toward the Ultimate Efficiency and Practicability
    • Place of Presentation
      滋賀
    • Year and Date
      2008-05-27
    • Related Report
      2008 Annual Research Report
  • [Presentation] バナジウム錯体触媒を用いた環境調和型酸化反応の開発2008

    • Author(s)
      小川 昭弥
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Year and Date
      2008-03-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] 重希土金属を用いた光還元系の開発2007

    • Author(s)
      小川 昭弥
    • Organizer
      第54回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      新潟
    • Year and Date
      2007-12-01
    • Related Report
      2007 Annual Research Report
  • [Presentation] バナジウム錯体触媒による環境調和型酸化反応の開発2007

    • Author(s)
      小川 昭弥
    • Organizer
      第40回酸化反応討論会
    • Place of Presentation
      奈良
    • Year and Date
      2007-11-18
    • Related Report
      2007 Annual Research Report
  • [Presentation] Atom-economical bisthiolation and bisselenation of allenes catalyzed byrakis(triphenylphosphine)palladium(0)2007

    • Author(s)
      小川 昭弥
    • Organizer
      Intemaational Conference on Asymmetric Organocatalysis
    • Place of Presentation
      滋賀
    • Year and Date
      2007-05-28
    • Related Report
      2007 Annual Research Report
  • [Book] Tetraphenyldiphosphine. In Electronic Encyclopedia of Reagents for Organic Synthesis ; Paquette, L. A.; Fuchs, Philip L.; Crich, D.; M olander, G. (Eds.)2008

    • Author(s)
      Ogawa A., 他3名
    • Publisher
      John Wiley & Sons(On line)
    • Related Report
      2008 Annual Research Report
  • [Book] Carbonylation of Allenes In Modern Carbonylation Methods ; Kollar, L. (Ed.)2008

    • Author(s)
      Nomoto A.; Ogawa A.
    • Total Pages
      10
    • Publisher
      Wiley-VCH
    • Related Report
      2008 Annual Research Report
  • [Book] Handbook of Reagents for Organic Synthesis, ed by L.Paquette2007

    • Author(s)
      Nomoto A., Ogawa, A.
    • Publisher
      John Wiley & Sons
    • Related Report
      2007 Annual Research Report
  • [Book] Handbook of Reagents for Organic Synthesis, ed by L.Paquette2007

    • Author(s)
      Tsuchii K., Ogawa, A.
    • Publisher
      John Wiley & Sons
    • Related Report
      2007 Annual Research Report
  • [Remarks]

    • URL

      http://www.chem.osakafu-u.ac.jp/ohka/ohka8/research.html

    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.iao.osakafu-u.ac.jp/ipbc/fea2007_Postor/12%20nomoto_a.pdf

    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.osakafu-u.ac.jp/research/pdf/map.pdf

    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://www.iao.osakafu-u.ac.jp/ipbc/fea2007_postor/12%20nomoto_a.pdf

    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] カルボニル化合物の製造方法

    • Inventor(s)
      小川昭弥、他2名
    • Industrial Property Rights Holder
      大阪府立大学
    • Related Report
      2007 Annual Research Report
  • [Patent(Industrial Property Rights)] アミン化合物の酸化方法及びイミン化合物製造方法

    • Inventor(s)
      小川昭弥、他2名
    • Industrial Property Rights Holder
      大阪府立大学
    • Related Report
      2007 Annual Research Report

URL: 

Published: 2007-04-01   Modified: 2018-03-28  

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