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Development of Practical Electron Transfer Driven Reactions for Organic Synthesis

Research Project

Project/Area Number 11555242
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field Synthetic chemistry
Research InstitutionKYOTO UNIVERSITY

Principal Investigator

YOSHIDA Jun-ichi  Graduate School of Engineering, Kyoto University, Professor, 工学研究科, 教授 (30127170)

Co-Investigator(Kenkyū-buntansha) SUGA Seiji  Graduate School of Engineering, Kyoto University, Professor, 工学研究科, 講師 (50291430)
Project Period (FY) 1999 – 2001
Project Status Completed (Fiscal Year 2001)
Budget Amount *help
¥13,500,000 (Direct Cost: ¥13,500,000)
Fiscal Year 2001: ¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2000: ¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 1999: ¥6,200,000 (Direct Cost: ¥6,200,000)
KeywordsElectron Transfer / Cation Pool Method / Cation Flow Method / Combinetorial Synthesis / 電子移動駆動型反応 / 炭素カチオン / 炭素求核剤 / 炭素-炭素結合形成 / 炭素―炭素結合形成
Research Abstract

We aimed to develop a practical electron transfer driven reaction for organic synthesis, and a "cation flow"method has been developed on the basis of the "cation pool" method. In the "cation flow" method, carbocations generated using a low temperature electrochemical microflow reactor were immediately trapped with carbon nucleophies. Downsizing of a electrochemical flow reactor enables efficient temperature control and shortening ofa residence time, and thus an application of this system to less stable carbocation could be possible. We have also developed a direct analysis system of the flow of the carbocations using FITR spectrometer. More outstanding feature of the "cation flow" system is that continuous sequential combinatorial synthesis can be accomplished by simple flow switching. Although parallel syntheses enjoy versatile applications in combinatorial chemistry, the present continuous sequential method opens a new intriguing aspect of combinatorial synthesis.

Report

(4 results)
  • 2001 Annual Research Report   Final Research Report Summary
  • 2000 Annual Research Report
  • 1999 Annual Research Report
  • Research Products

    (29 results)

All Other

All Publications (29 results)

  • [Publications] Jun-ichi Yoshida: "Basic Concepts of "Cation Pool" and "Cation Flow" Methods and Their Applications in Conventional and Combinatorial Organic Synthesis"Chemistry a European Journal. (印刷中).

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: "Reduction of a "Cation Pool". A New Approach to Radical Mediated C-C Bond Formation"Journal of the American Chemical Society. 124. 30-31 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: ""Cation Flow" Method. A New Approach to Conventional and Combinatorial Organic Syntheses Using Electrochemical Microflow Systems"Journal of the American Chemical Society. 123. 7941-7942 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: "Reaction of electrogenerated "Iminium Cation Pool" with organometallic Reagents. Direct Oxidative α-Alkylation and -Arylation of Amine Derivatives"Tetrahedron Letters. 42. 2173-2176 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 吉田 潤一: "カチオンプール法 -不安定なカルボカチオンを蓄え、そして反応させる-"現代化学. 7月号. 36 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] 吉田 潤一: "電子移動場での有機反応"「有機合成化学の新潮流」季刊化学総説. 47. 138-148 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: "Basic Concepts of "Cation Pool" and "Cation Flow" Methods and Their Applications in Conventional and Combinatorial Organic Synthesis"Chemistry a European Journal. (in press).

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: "Reduction of a "Cation Pool". A New Approach to Radical Mediated C-C Bond Formation"Journal of the American Chemical Society. 124. 30-31 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: ""Cation Flow" Method. A New Approach to Conventional and Combinator ial Organic Syntheses Using Electrochemical Microflow Systems"Journal of the American Chemical Society. 123. 7941-7942 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: "Reaction of Electrogenerated "Irainium Cation Pool" with Organometal lie Reagents. Direct Oxidative a-Alkylation and -Arylation of Araine Derivatives"Tetrahedron Letters. 42. 2173-2176 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: "Cation Pool Method. Accumulation and Reactions of Reactive Carbocation Intermediate"Gendaikagaku. 7. 36 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: "Electron Transfer Driven Organic Reactions""New Trends in Synthetic Organic Chemistry" Kikankagakusousetsu. 47. 138-148 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2001 Final Research Report Summary
  • [Publications] Jun-ichi Yoshida: "Basic Concepts of "Cation Pool" and "Cation Flow" Methods and Their Applications in Conventional and Combinatorial Organic Synthesis"Chemistry a European Journal(印刷中).

    • Related Report
      2001 Annual Research Report
  • [Publications] Jun-ichi Yoshida: "Reduction of a "Cation Pool" A New Approach to Radical Mediated C-C Bond Formation"Journal of the American Chemical Society. 124. 30-31 (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] Jun-ichi Yoshida: ""Cation Flow" Method, A New Approach to Conventional and Combinatorial Organic Syntheses Using Electrochemical Microflow Systems"Journal of the American Chemical Society. 123. 7941-7942 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Jun-ichi Yoshida: "Reaction of Electrogenerated "Iminium Cation Pool" with Organometallic Reagents. Direct Oxidative α-Alkylation and Arylation of Amine Derivatives"Tetrahedron Letters. 42. 2173-2176 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 吉田潤一: "カチオンプール法-不安定なカルボカチオンを蓄え、そして反応させる-"現代化学. 7月号. 36 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 吉田潤一: "電子移動場での有機反応"「有機合成化学の新潮流」季刊化学総説. 47. 138-148 (2000)

    • Related Report
      2001 Annual Research Report
  • [Publications] S.Suga,J.Yoshida, et.al.: "Reaction of Electrogenerated "Iminium Cation Pool" with Organometallic Reagents. Direct Oxidative α-Alkylation and -Arylation of Amine Derivatives"Tetrahedron Lett.. 42. 2173-2176 (2001)

    • Related Report
      2000 Annual Research Report
  • [Publications] M.Sugawara and J.Yoshida: "Stereoselective Cyclopropylmethylation Reactions of Homoallylstannanes with Carbon Electrophiles"Tetrahedron. 56. 4683-4689 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Itami,J.Yoshida, et.al.: "Highly Efficient Carbopalladation across Vinylsilane : Dual Role of 2-PyMe_2Si Group as a Directing Group and as a Phase Tag"JAm.Chem.Soc.. 122. 12013-12014 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] M.Sugawara and J.Yoshida: "Evaluation of the Relative Magnitude of the β-Effect of Silicon and the γ-Effect of Tin by Intermolecular Competition"Bull.Chem.Soc.Jpn.. 73. 1253-1257 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] K.Itami,J.Yoshida, et.al.: "[Bis(2-pyridyldimethylsilyl)methyl]lithium.New Reagent for the Stereoselective Synthesis of Vinylsilanes"Org.Lett.. 2. 1299-1302 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] M.Watanabe,J.Yoshida,et.al.: "Intramolecular Assistance of Electron Transfer from Heteroatom Compounds.Electrochemical Oxidation of 2-(2-Pyridyl) ethyl-Substituted Ethers, Sulfides, and Selenides"Bull. Chem. Soc. Jpn.. 73. 243-247 (2000)

    • Related Report
      1999 Annual Research Report
  • [Publications] J.Yoshida et al.: "Direct Oxidative Carbon-Carbon Bond Formation Using the "Cation Pool" Method.1.Generation of Iminium Cation Pools and Their Reaction with Carbon Nucleophiles"J. Am. Chem. Soc.. 121. 9546-9549 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] K.Itami,J.Yoshida et.al.: "Oxidation of 2-Pyridyldimethylsilyl Group to Hydroxyl Group by H2O2/KF. Implication of Fluoride Ion Accelerated 2-Pyridyl-Silyl Bond Cleavage"J. Org. Chem.. 64. 8709-8714 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] J.Yoshida et al.: "(2-Pyridylsilyl) Group as a Multifunctional "Phase Tag" for Solution Phase Synthesis"Tetrahedron Lett.. 40. 3403-3406 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] J.Yoshida et al.: "2-(2-Pyridyl) ethylsilyl Groups as a New Class of Electroauxiliary Fine Tuning of the Electron Transfer Driven Reactions by the Dynamic Coordination to Silicon"Chem. Lett.,. 251-252 (1999)

    • Related Report
      1999 Annual Research Report
  • [Publications] S.Suga,J.Yoshida et.al.: "General and Efficient Method for the Synthesis of Alkoxymethylsilanes"J. Applied Organometal. Chem.. 13. 469-474 (1999)

    • Related Report
      1999 Annual Research Report

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Published: 1999-04-01   Modified: 2016-04-21  

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