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New Low Valent Titanium Reagents and Their Application to Bond-Forming and-Cleaving Reactions

Research Project

Project/Area Number 19550113
Research Category

Grant-in-Aid for Scientific Research (C)

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

Principal Investigator

OKAMOTO Sentaro  Kanagawa University, 工学部, 教授 (00201989)

Project Period (FY) 2007 – 2008
Project Status Completed (Fiscal Year 2008)
Budget Amount *help
¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000)
Fiscal Year 2008: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2007: ¥2,990,000 (Direct Cost: ¥2,300,000、Indirect Cost: ¥690,000)
Keywords有機金属触媒 / 低原子価チタン / 脱アリル化 / 脱プロパルギル化 / アルキン[2+2+2]環化付加 / McMurry反応 / 置換ベンゼン / エポキシドラジカル解裂 / ラジカル環化反応 / 脱保護法
Research Abstract

チタンアルコキシド[Ti(OR)_4]と金属Mg粉末が少量のハロゲン源[Me_3SiClやMgBr_2など]の存在下で反応し、低原子価チタン反応剤を温和に発生すること、および、この反応剤によって種々の結合生成反応や結合解裂反応が進行することを見いだした。(i) アリルエーテル、プロパルギルエーテルの切断、(ii) アルキンの[2+2+2]型環化付加反応、(iii) 室温付近で均一系として使用できるMcMurry反応剤、(iv) イミンの1,2-ジアミンへの還元的二量化剤、(v) エポキシドのC-O結合をラジカル的に解裂し、(vi) その生じるラジカルによってアルケンとの分子内環化反応が進行した。

Report

(3 results)
  • 2008 Annual Research Report   Final Research Report ( PDF )
  • 2007 Annual Research Report
  • Research Products

    (20 results)

All 2009 2008 2007 Other

All Journal Article (7 results) (of which Peer Reviewed: 7 results) Presentation (10 results) Remarks (3 results)

  • [Journal Article] Two-step allylic carbon insertion between ketone carbonyl and carbons giving α-quaternary α-vinyl ketones2008

    • Author(s)
      Jing-Qian He, Daisuke Shibata, Chihaya Ohno, Sentaro Okamoto
    • Journal Title

      Tetrahedron Letters Vol.49

      Pages: 6724-6727

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Copper-catalyzed intramolecular hydroamination of allenylamines to 3-pyrrolines or 2-alkenylpyrrolidines2008

    • Author(s)
      Akiko Tsuhako, Daisuke Oikawa, Kazushi Sakai, Sentaro Okamoto
    • Journal Title

      Tetrahedron Letters Vol.49

      Pages: 6529-6532

    • NAID

      120002756168

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Two-step allylio carbon insertion between ketone carbonyl and carbons giving α-quaternary α-vinyl ketones2008

    • Author(s)
      Jing-Qiau He, Daisuke Shibata, Chihaya Ohno, Sentaro Okamoto
    • Journal Title

      Tetrahedron Letters 49

      Pages: 6724-6727

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-catalyzed intramolecular hydroamination of allenylamines to 3-pyrrolines or 2-alkenylpyrrolidines2008

    • Author(s)
      Akiko Tsuhako, DaAsuke Oikawa, Kazushi Sakai, Sentaro Okamoto
    • Journal Title

      Tetrahedron Letters 49

      Pages: 6529-6532

    • NAID

      120002756168

    • Related Report
      2008 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Carbonyl reduction with CaH_2 and R_3SiCl catalyzed by ZnCl_22007

    • Author(s)
      Akiko Tsuhako, Jing-Qian He, Mariko Mihara, Naoko Saino and Sentaro Okamoto
    • Journal Title

      Tetrahedron Letters Vol.48

      Pages: 9120-9123

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Selective Cleavage of Allyl and Propargyl Ethers to Alcohols Catalyzed by Ti(O-i-Pr)_4/MXn/Mg2007

    • Author(s)
      Mutsumi Ohkubo, Sayaka Mochizuki, Takeshi Sano, Yuuki Kawaguchi, SentaroOkamoto
    • Journal Title

      Organic Letters Vol.9

      Pages: 733-776

    • Related Report
      2008 Final Research Report
    • Peer Reviewed
  • [Journal Article] Carbonyl reduction with CaH_2 and R_3SiCl catalyzed by ZnCl_22007

    • Author(s)
      Akiko Tsuhako, Jing-Qian He, Mariko Mihara, Naoko Saino and Sentaro Okamoto
    • Journal Title

      Tetrahedron Letters 47

      Pages: 9120-9123

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Presentation] 低原子価チタン反応剤Ti(O-i-Pr)_4/TMSCl/Mgとエポキシドとの反応2009

    • Author(s)
      何せいせい, 丹羽亮介, 大野千隼, 松野千加士, 岡本専太郎
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部(千葉)
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] 低原子価チタン反応剤Ti(O-i-Pr)_4/TMSCl/MgのMcMurryカップリングへの適用2009

    • Author(s)
      大野千隼, 何せいせい, 大岩裕志, 松野千加士, 岡本専太郎
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部(千葉)
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] CaH_2/ZnX_2反応剤による還元反応2009

    • Author(s)
      河治健, 境勇三, 何せいせい, 岡本専太郎
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      日本大学理工学部(千葉)
    • Year and Date
      2009-03-29
    • Related Report
      2008 Annual Research Report
  • [Presentation] 低原子価チタン反応剤Ti(O-i-Pr)_4/TMSCl/Mgとエポキシドとの反応2009

    • Author(s)
      何せいせい・丹羽亮介・大野千隼・松野千加士・岡本専太郎
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Related Report
      2008 Final Research Report
  • [Presentation] 低原子価チタン反応剤Ti(O-i-Pr)_4/TMSCl/MgのMcMurryカップリングへの適用2009

    • Author(s)
      大野千隼・何せいせい・大岩裕志・松野千加士・岡本専太郎
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Related Report
      2008 Final Research Report
  • [Presentation] CaH_2/ZnX_2反応剤による還元反応2009

    • Author(s)
      河治健・境勇三・何せいせい・岡本専太郎
    • Organizer
      日本化学会第89春季年会
    • Place of Presentation
      千葉
    • Related Report
      2008 Final Research Report
  • [Presentation] カルシウムヒドリドによるカルボニル化合物の還元反応2008

    • Author(s)
      津波古亜希子・何せいせい・三原真梨子・才野直子・岡本専太郎
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      立教大学
    • Year and Date
      2008-03-29
    • Related Report
      2007 Annual Research Report
  • [Presentation] カルシウムヒドリドによるカルボニル化合物の還元反応2008

    • Author(s)
      津波古亜希子, 何せいせい, 三原真梨子, 才野直子, 岡本専太郎
    • Organizer
      日本化学会第88春季年会
    • Place of Presentation
      東京
    • Related Report
      2008 Final Research Report
  • [Presentation] Use of CaH_2 as A Reductive Hydride Source for Reduction of Ketones, Aldehydes and Imines2007

    • Author(s)
      Akiko Tsuhako, Mariko Mihara, Toshio Aida, Norikatsu Kuboki, Kenji Kato, Chikashi Matsuno and Sentaro Okamoto
    • Organizer
      第54回有機金蔵化学討論会
    • Place of Presentation
      広島大学
    • Year and Date
      2007-10-27
    • Related Report
      2007 Annual Research Report
  • [Presentation] Use of CaH_2 as A Reductive Hydride Source for Reduction of Ketones, Aldehydes and Imines2007

    • Author(s)
      Akiko Tsuhako, Mariko Mihara, Toshio Aida, Norikatsu Kuboki, Kenji Kato, Chikashi Matsuno and Sentaro Okamoto
    • Organizer
      54^<th> Symposium on Organometallic Chemistry
    • Place of Presentation
      Hiroshima
    • Related Report
      2008 Final Research Report
  • [Remarks] 研究室HP

    • URL

      http://apchem2.kanagawa-u.ac.jp/~okamotolab/index.html

    • Related Report
      2008 Final Research Report
  • [Remarks]

    • URL

      http://apchem2.kanagawa-u.ac.jp/~okamotolab/index.html

    • Related Report
      2008 Annual Research Report
  • [Remarks]

    • URL

      http://apchem2.kanagawa-u.ac.jp/~okamotolab/index.html

    • Related Report
      2007 Annual Research Report

URL: 

Published: 2007-04-01   Modified: 2016-04-21  

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