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Development of Indium-and Platinum-catalyzed Reactions for Environmentally Benign Organic Synthesis

Research Project

Project/Area Number 17550094
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionUniversity of Tsukuba

Principal Investigator

MIURA Katsukiyo  University of Tsukuba, Graduate School of Pure and Applied Sciences, Associate Professor (20251035)

Co-Investigator(Kenkyū-buntansha) HOSOMI Akira  University of Tsukuba, Professor Emeritus (00004440)
Project Period (FY) 2005 – 2007
Project Status Completed (Fiscal Year 2007)
Budget Amount *help
¥3,930,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥330,000)
Fiscal Year 2007: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2006: ¥900,000 (Direct Cost: ¥900,000)
Fiscal Year 2005: ¥1,600,000 (Direct Cost: ¥1,600,000)
KeywordsPlatinum / Indium / Environmentally Benign Synthesis / Silicon Reagent / Allylation / Cyclic Ether / Radical Reaction / Conjugated Enone / ビニルシラン / アリルシラン / α,β-不飽和ケトン / アルキン / パラジウム / 二官能基化 / クロスカップリング / タンデム反応 / エン型反応 / 触媒反応 / ヒドロシラン / ラジカル反応 / シリルエノラート
Research Abstract

We have developed new reactions using platinum and indium catalysts for environmentally benign organic synthesis as shown below.
1. Allylation of Carbon Electrophiles with Vinylsilanes: It was found that vinylsilanes were smoothly isomerized to allylsilanes under catalysis by platinum salts. This isomerization was successfully utilized for allylation of carbon electrophiles with vinylsilanes, which is more convenient than the known method using allylsilanes because of easy access to vinylsilanes.
2. Annulation between Alkenols and Aldehydes: In the presence of catalytic amounts of PtCl_2 and AgOTf, 5-methyl-5-hexen-1-ols reacted efficiently with aldehydes to give tetrahydropyrans (THPs). This annulation is useful for atom-economical, stereoselective synthesis of multi-substituted THPs.
3. Allylation of Acetals with Alkenes: The PtCl_2-AgX catalyst system enabled an ene-type allylation of acetals with 1, 1-disubstituted alkenes. This allylation provides a convenient, direct route to homoallyl ethers.
4. Radical Reactions of Haloalkanes with Hydrosilanes: It was found that a catalytic amount of In (Oac)_3 effectively promoted radical reduction of haloalkanes with PhSiH_3 under very mild reaction conditions. The In (Oac)_3-PhSiH_3 system was successfully utilized for radical addition of haloalkanes to alkenes. The present method is environmentally more benign than the known method using toxic organotin hydrides.
5. Carbonyl Metathesis-type Reaction of Alkynes with Aldehydes: The In (Otf)_3-catalyzed reaction of arylalkynes with aromatic aldehydes gave chalcones in good yield. The carbonyl metathesis-type reaction could be applied to an efficient cyclization of alkynals.

Report

(4 results)
  • 2007 Annual Research Report   Final Research Report Summary
  • 2006 Annual Research Report
  • 2005 Annual Research Report
  • Research Products

    (40 results)

All 2008 2007 2006 2005 2003

All Journal Article (21 results) (of which Peer Reviewed: 2 results) Presentation (17 results) Book (2 results)

  • [Journal Article] Silicon Lewis Acids2008

    • Author(s)
      三浦勝清
    • Journal Title

      New Acid Catalysis in Modern Organic Synthesis ed. By H. Yamamoto and K. Ishihara", Vol.1, " Chap.9", Elsevier," Amsterdam

      Pages: 469-516

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Indium(III) Acetate-Catalyzed Intermolecular Radical Addition of Organic Iodides to Electron-deficient Alkenes2008

    • Author(s)
      K. Miura, M. Tomita, J. Ichikawa, and A. Hosomi
    • Journal Title

      Org. Lett. 10(1)

      Pages: 133-136

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Platinum(II)-Catalyzed Annulation of 5-Methyl-5-hexen-1-ols with Aldehydes2008

    • Author(s)
      K. Miura, M. Horiike, G. Inoue, J. Ichikawa, and A. Hosomi
    • Journal Title

      Chem. Lett. 37(3)

      Pages: 270-271

    • NAID

      10021078202

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Silicon Lewis Acids2008

    • Author(s)
      K. Miura and A. Hosomi
    • Journal Title

      New Acid Catalysis in Modern Organic Synthesis ed. by H. Yamamoto and K. Ishihara, Wiley-VCH, Weinheim, Germany Vol.1, Chap.9

      Pages: 469-516

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Indium(III)Acetate-Catalyzed Intermolecular Radical Addition of Organic Iodides to Electron-deficient Alkenes2008

    • Author(s)
      三浦 勝清
    • Journal Title

      Organic Letters 10

      Pages: 133-136

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Platinum(II)-Catalyzed Annulation of 5-Methyl-5-hexen-1-ols with Aldehydes2008

    • Author(s)
      三浦 勝清
    • Journal Title

      Chemistry Letters 37

      Pages: 270-271

    • NAID

      10021078202

    • Related Report
      2007 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Silicon Lewis Acids2008

    • Author(s)
      三浦 勝清
    • Journal Title

      Silicon Lewis Acids in New Acid Catalysis in Modern Organic Synthesis, Wiley-VCH

      Pages: 469-516

    • Related Report
      2007 Annual Research Report
  • [Journal Article] Silicon2007

    • Author(s)
      三浦勝清
    • Journal Title

      Comprehensive Organometallic Chemistry III ed. by R. H. Crabtree and M.p. Mingos", Vol.9, " Chap.7.", Elsevier," Amsterdam

      Pages: 297-339

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Silicon2007

    • Author(s)
      K. Miura and A. Hosomi
    • Journal Title

      Comprehensive Organometallic Chemistry III ed. by R. H. Crabtree and M. P. Mingos, Elsevier, Amsterdam Vol.9, Chap.7

      Pages: 297-339

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Indium-Catalyzed Radical Reductions of Organic Halides with Hydrosilanes2007

    • Author(s)
      K. Miura, M. Tomita, Y. Yamada, and A. Hosomi
    • Journal Title

      J. Org. Chem. 72(3)

      Pages: 787-792

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Homolytic Hydrogermylation of Alkenes with Dibutylchlorogermane2007

    • Author(s)
      三浦 勝清
    • Journal Title

      Journal of Organometallic Chemistry 692巻1-3号

      Pages: 514-519

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Indium-Catalyzed Radical Reductions of Organic Halides with Hydrosilanes2007

    • Author(s)
      三浦 勝清
    • Journal Title

      The Journal of Organic Chemistry 72巻3号

      Pages: 787-792

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Indium(III) Salt-Promoted Intramolecular Addition of Allylsilanes to Alkynes2006

    • Author(s)
      K. Miura, N. Fujisawa, S. Toyohara, and A. Hosomi
    • Journal Title

      Synlett 12

      Pages: 1883-1886

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Indium(III)Salt-Promoted Intermolecular Addition of Allylsilanes to Alkynes2006

    • Author(s)
      三浦 勝清
    • Journal Title

      Synlett 12号

      Pages: 1883-1886

    • Related Report
      2006 Annual Research Report
  • [Journal Article] Platinum(II)Salt-Catalyzed Annulation of Hydroxyalkyl-Substituted Vinylsilanes with Aldehydes2005

    • Author(s)
      K. Miura, R. Itaya, M. Horiike, H. Izumi, and A. Hosomi
    • Journal Title

      Synlett 20

      Pages: 3148-3150

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Journal Article] Highly Regio- and Stereoselective Hydrostannylation of Propargyl Alcohols and Ethers Using Dibutylchlorostannane and Lithium Chloride2005

    • Author(s)
      三浦 勝清
    • Journal Title

      Synlett 3号

      Pages: 406-410

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Highly Regio- and Stereoselective Hydrostannylation of Alkynols with A New Lewis Acidic Hydrostannane2005

    • Author(s)
      三浦 勝清
    • Journal Title

      Organic Letter 7巻3号

      Pages: 503-506

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Highly Diastereoselective Hydrostannylation of Allyl and Homoallyl Alcohols with Dibutyl(trifluoromethanesulfoxy)stannane2005

    • Author(s)
      三浦 勝清
    • Journal Title

      Journal of the American Chemical Society 127巻26号

      Pages: 9366-9367

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Metal Chloride-Promoted Aldol Reaction of α-Dimethylsilylesters with Aldehydes, Ketones, and α-Enones2005

    • Author(s)
      三浦 勝清
    • Journal Title

      Synlett 12号

      Pages: 1917-1921

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Synthetic Radical Reactions Using Dibutylchlorogermane and Dibutylethoxygermane as Radical Mediators2005

    • Author(s)
      三浦 勝清
    • Journal Title

      Synlett 20号

      Pages: 3151-3153

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Platinum(II) Salt-Catalyzed Annulation of Hydroxyalkyl-Substituted Vinylsilanes with Aldehydes2005

    • Author(s)
      三浦 勝清
    • Journal Title

      Synlett 20号

      Pages: 3148-3150

    • Related Report
      2005 Annual Research Report
  • [Presentation] Platinum(II)-Catalyzed Reaction of Vinylsilanes with Aldehydes. Investigation of Scope and Reaction Mechanism2008

    • Author(s)
      K. Miura, G. Inoue, J. Ichikawa, and A. Hosomi
    • Organizer
      88th Spring Meeting of the Chemical Society of Japan
    • Place of Presentation
      Rikkyo University, Ikebukuro
    • Year and Date
      2008-03-26
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Platinum(II)-Catalyzed Reaction of Vinylsilanes with Carbon Electrophiles2007

    • Author(s)
      K. Miura, G. Inoue, J. Ichikawa, and A. Hosomi
    • Organizer
      54th Symposium on Organometallic Chemistry
    • Place of Presentation
      Hiroshima University, Higashi-hiroshima
    • Year and Date
      2007-10-28
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] 2価白金触媒によるビニルシランと炭素求電子剤の反応2007

    • Author(s)
      三浦 勝清
    • Organizer
      第54回有機金属化学討論会
    • Place of Presentation
      広島
    • Year and Date
      2007-10-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] Platinum(II)-Catalyzed Addition of Vinylsilanes to Carbon Electrophiles2007

    • Author(s)
      K. Miura, G. Inoue, and A. Hosomi
    • Organizer
      International Conference on Asymmetric Organocatalysis
    • Place of Presentation
      Ootsu
    • Year and Date
      2007-05-28
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Platinum(II)-Catalyzed Addition of Vinylsilanes to Carbon Electrophiles2007

    • Author(s)
      三浦 勝清
    • Organizer
      International Conference on Asymmetric Organocatalysis
    • Place of Presentation
      大津
    • Year and Date
      2007-05-28
    • Related Report
      2007 Annual Research Report
  • [Presentation] Platinum-Catalyzed Allylation of Carbon Electrophiles with Vinylsilanes2007

    • Author(s)
      K. Miura, G. Inoue, and A. Hosomi
    • Organizer
      87th Spring Meeting of the Chemical Society of Japan
    • Place of Presentation
      Kansai University, Suita
    • Year and Date
      2007-03-27
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Platinum-Catalyzed Alcoholysis of Vinylsilanes2007

    • Author(s)
      K. Miura, H. Izumi, and A. Hosomi
    • Organizer
      87th Spring Meeting of the Chemical Society of Japan
    • Place of Presentation
      Kansai University, Suita
    • Year and Date
      2007-03-27
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Indium-Catalyzed Carbonyl Metathesis-type Reaction of Alkynes with Aldehydes2007

    • Author(s)
      K. Miura, K. Ito, and A. Hosomi
    • Organizer
      87th Spring Meeting of the Chemical Society of Japan
    • Place of Presentation
      Kansai University, Suita
    • Year and Date
      2007-03-26
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Indium-Catalyzed Radical Reduction and Radical Addition of Haloalkanes2007

    • Author(s)
      K. Miura, M. Tomita, and A. Hosomi
    • Organizer
      4th International Symposium on Future-Oriented Interdisciplinary Materials Science
    • Place of Presentation
      Tsukuba
    • Year and Date
      2007-03-12
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Indium(III) Salt-Catalyzed Reaction of Alkynes with Aldehydes Forming Conjugated Enones2006

    • Author(s)
      K. Miura, K. Ito, A. Yamanobe, and A. Hosomi
    • Organizer
      10th International Kyoto Conference on New Aspects of Organic Chemistry(IKCOC-10)
    • Place of Presentation
      Kyoto
    • Year and Date
      2006-11-16
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Platinum-Catalyzed Nucleophilic Addition of Vinylsilanes at the β-Position2006

    • Author(s)
      K. Miura, G. Inoue, H. Izumi, and A. Hosomi
    • Organizer
      53rd Symposium on Organometallic Chemistry
    • Place of Presentation
      Osaka City University, Osaka.
    • Year and Date
      2006-09-08
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Indium-Catalyzed Intramolecular Addition of Alkynes to Aldehydes2006

    • Author(s)
      K. Miura, A. Yamanobe, and A. Hosomi
    • Organizer
      86th Spring Meeting of the Chemical Society of Japan
    • Place of Presentation
      Nihon University, Funabashi
    • Year and Date
      2006-03-28
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] New Synthetic Reactions Using Organosilicon Reagents under Catalysis by Indium(III) Salts2005

    • Author(s)
      K. Miura
    • Organizer
      The 2005 International Chemical Congress of Pacific Basin Societies
    • Place of Presentation
      Honolulu, Hawaii, USA.
    • Year and Date
      2005-12-16
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Activation of Alkynes by Indium Salts and Its Application to Catalytic C-C Bond Formation2005

    • Author(s)
      K. Miura, S. Toyohara, and A. Hosomi
    • Organizer
      32nd Symposium on Heteroatom Chemistry
    • Place of Presentation
      Tsukuba
    • Year and Date
      2005-12-05
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Platinum(II)-Catalyzed Reactions of Aldehydes and Acetals with Alkenes2005

    • Author(s)
      K. Miura. M. Horiike, H. Izumi, and A. Hosomi
    • Organizer
      52nd Symposium on Organometallic Chemistry
    • Place of Presentation
      Doshisha University, Kyoutanabe
    • Year and Date
      2005-09-15
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Indium-Catalyzed Radical Reduction and Radical Addition of Haloalkanes2005

    • Author(s)
      K. Miura. M. Tomita, and A. Hosomi
    • Organizer
      32nd Symposium on Heteroatom Chemistry
    • Place of Presentation
      Tsukuba
    • Year and Date
      2005-09-05
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Presentation] Platinum-Catalyzed Nucleophilic Addition of Vinylsilanes to Aldehydes at the β-Position2003

    • Author(s)
      K. Miura, G. Inoue, and A. Hosomi
    • Organizer
      86th Spring Meeting of the Chemical Society of Japan
    • Place of Presentation
      Nihon University, Funabashi
    • Year and Date
      2003-03-27
    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2007 Final Research Report Summary
  • [Book] Silicon Lewis Acidsin New Acid Catalysis in Modern Organic Synthesis2008

    • Author(s)
      三津勝清
    • Publisher
      Wiley-VCH
    • Related Report
      2007 Annual Research Report
  • [Book] "Silicon" in Comprehensive Organometallic Chemistry III ed.by R.H.Crabtree and M.P.Mingos,Vol.9,Chap.7.2006

    • Author(s)
      三浦 勝清
    • Total Pages
      42
    • Publisher
      Elsevier
    • Related Report
      2006 Annual Research Report

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Published: 2005-04-01   Modified: 2016-04-21  

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