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Development of Sustainable Highly Selective Electrofluorination Using Electrocatalysis

Research Project

Project/Area Number 12555252
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 有機工業化学
Research InstitutionTokyo Institute of Technology

Principal Investigator

FUCHIGAMI Toshio  Tokyo Institute of Technology, Professor Interdisciplinary Graduate School of Science and Engineering, 大学院・総合理工学研究科, 教授 (10016701)

Co-Investigator(Kenkyū-buntansha) ATOBE Mahito  Interdisciplinary Graduate School Lecturer of Science and Engineering, 大学院・総合理工学研究科, 講師 (90291351)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥8,900,000 (Direct Cost: ¥8,900,000)
Fiscal Year 2002: ¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 2001: ¥2,500,000 (Direct Cost: ¥2,500,000)
Fiscal Year 2000: ¥3,900,000 (Direct Cost: ¥3,900,000)
KeywordsElectrocatalysis / Mediator / Triarylamine / Diamonde electrode / Bio active compound / Electrochemical fluorination / Fluorodesulfurization / Organic electrolyte for Libattery / メデイエーター / 生理活性物質 / ベンゾイルフルオリド / 複素環化合物 / 含フッ素β-ラクタム / ジフルオロメチレン基 / 含フッ素環状カーボナート / 含フッ素エーテル / リチウム電池 / 有機電解液 / モノフルオロ化合物 / ジフルオロ化合物
Research Abstract

Selective fluorination of organic compounds is highly useful for development of medicines, agrochemicals, and functional materials. However, the fluorination methods have not been well developed. Therefore, we aimed the following projects through the new development of sustainable highly selective electrofluorination using electrocatalysis.
1) Development of organic electrolytes for high performance rechargeable Li batteries
2) Development of fluorinated biologically active compounds usinig electrocatalytic fluorodesulfurization
3) Selective electrofluorination of organic compounds using diamonds electrodes
4) Development of fluorinated ethers as flon substituents
We have mostly achieved above projects and the results seem to be useful for future study on selective fluorination of various organic molecules.

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (37 results)

All Other

All Publications (37 results)

  • [Publications] HIDEKI ISHII: "Highly selective anodic monofluorination of 4-arylthio-1,3-dioxolan-2-ones : a marked solvent effect on product selectivity"Chemical Communications. 1617-1618 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] MOHAMED R.SHAABAN: "Marked Solvent Effects on Regioselective Anodic Monofluorination of 4-Oxo-2-pyrimidyl Sulfides"Journal of Organic Chemistry. 65. 8685-8689 (2000)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] TOSHIO FUCHIGAMI: "Anodic gem-Difluorodesulfurization Using Triarylamine Mediators"Journal of Electroanalytical Chemistry. 507. 30-33 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] TOSHIO FUCHIGAMI: "Indirect Anodic Monofluorodesulfurization of β-Phenylsulfenyl β-lactams Using a Triarylamine Mediator"Synlett.. 1269-1271 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] DAISUKE BABA: "Regio-and Diastereoselective Anodic Fluorination of Thiazolidines"Journal of Organic Chemistry. 66. 7020-7024 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] TOSHIKI TAJIMA: "A Facile Synthesis of gem-Difluorinated Heterocyclic Compounds Using Anodic Fluorination of 2-Cyano-1-methylpyrrole as a Key Step"Synthesis. 2597-2600 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] LYADH SAYED M.: "Anodic Mono-and Difluorination of Thiazolyl Sulfides"Journal of Organic Chemistry. 67. 9379-9383 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yi SHEN: "Indirect anodic fluorodesulfurization of s-aryl thiobenzoates using a triarylamine mediator"Journal of Electroanalytical Chemistry. 540. 189-194 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] TOSHIO FUCHIGAMI: "Highly Regio selective direct and indirect anodic monofluorination of heterocyclic compounds"Review of Heteroatom Chemistry. 19. 67-68 (1999)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 淵上寿雄: "メディエーター(電極触媒)を用いる有機電解合成"触媒. 44. 172-176 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] 淵上寿雄: "電極触媒科学の新展開"北大図書刊行会. 27 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] TOSHIO FUCHIGAMI: "Organic Electrochemistry, 4th Edition"Marcel Dekker. 16 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Hideki Ishii: "Highly Selective Anodic Monofluorination of 4-Arylthio-1,3-dioxolan-2-ones : A Marked Solvent Effect on Product Selectivity"J. Chem. Soc., Chem. Commun.. 1617-1618 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Mohamedo R. Shaaban: "Electrolytic Partial Fluorination of Organic Compounds. 42. Marked Solvent Effects on Regioselective Anodic Monofluorination of 4-Oxo-2-pyrimidyl Sulfides"J. Org. Chem.. 65. 8685-8689 (2000)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Toshio Fuchigami: "Electrolytic Partial Fluorination of Organic Compounds.44. Anodic gem-Difluoro desulfurization Using Triarylamine Mediators"J. Electroanal. Chem.. 507. 30-33 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Toshio Fuchigami: "Indirect Anodic Monofluorodesulfurization of β-Phenylsulfenyl β-lactams Using a Triarylamine Mediator"Synlett. 1269-1271 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Daisuke Baba: "Electrolytic Partial Fluorination of Organic Compound. 52. Regio- and Diastereoselective Anodic Fluorination of Thiazolidines"J. Org. Chem.. 66. 7020-7024 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Toshiki Tajima: "A Facile Synthesis of gem-Difluorinated Heterocyclic Compounds Using Anodic Fluorination of 2-Cyano-1-methylpyrrole as a Key Step"Synthesis (Special Topic). 2597-2600 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Sayed M. Sayed: "Electrolytic Partial Fluorination of Organic Compounds. Part 64. Anodic Mono- and Difluorination of Thiazolyl Sulfides"J. Org. Chem.. 67. 9379-9383 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Yi Shen: "Indirect Anodic Fluorodesulfurization of S-aryl Thiobenzoates Using a Triarylamine Mediator"J. Electroanal. Chem.. 540. 189-194 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Toshio Fuchigami: "Highly Regioselective Direct and Indirect Anodic Monofluorination of Heterocyclic Compounds"Rev. Heteroatom. Chem.. 19. 67-78 (1999)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Toshio Fuchigami: "Electroorganic Synthesis Using Mediators (Electrocatalysts)"Catalysts and Catalysis. 44. 172-176 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Toshio Fuchigami: "New Developments in Electrocatalysis Science"Hokkaido Univ. Library Publisher. 27 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] Toshio Fuchigami , ed. by H. Lund and O. Hammerich: ""Electrochemical Partial Fluorination" in "Organic Electrochemistry, 4th edition""Marcel Dekker. 16 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] RIYADH M.SAYED: "ANODIC MONO-AND DIFLVORINATION OF THIAZOLYL SULFID"JOURNAL OF ORGANIC CHEMISTRY. 67. 9379-9383 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] SHEN YI: "INDIRECT ANODIC FLUORODESUL FURIZATION OF S-ARYL TIOBENZOATES USING A TRIARYLAMINE MEDIATOR"JOURNAL OF ELECTROANALYTICAL CHEMISTRY. 540. 189-194 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] BABA DAISKE: "FLUORIDE ION MEDIATED ANOPIC METHOXYLATION AND ACETOXYCATION OF THIAZOLIDINES, 1,3-OXATHIOLANES, AND 1,3-DITHIOLANES"ELECTROCHIMICA ACTA. 48. 755-760 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 淵上 寿雄: "メデイエーター(電極触媒)を利用する有機電解合成"触媒. 44・3. 172-176 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] TOSHIO FUCHIGAMI: "ANODIC GEM-DIFLUORODESULFURIZATION USING TRIARYCAMINE MEDIATORS"JOURNAL OF ELECTROANALYTICAL CHEMISTRY. 507. 30-33 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] TOSHIO FUCHIGAMI: "INDIRECT ANODIC MONOFLUORODESULFURIZATION OF α-PHENYL-SULFENYL β-LACTAMS USING A TRIARYLAMINE MEDIATOR"SYNLETT. 8. 1269-1271 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] SAYED M, RIYADH: "HIGHLY REGIOSELECTIUE ANODIC MONO-AND DIFLUORINATION OF PROPARGYL SULFIDES AND PREPARATION OF α-FLUOROALLENYC SULFIDES"TETRAHEDRON LETTERS. 42. 3009-3011 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] KATSUTOSHI SUZUKI: "HIGHLY SELECTIUE ANODIC MONO-AND DIFLUORINATINO OF 4-PHENYLTHIOMETHYL-1, 3-DIOXOLAN-2-ONE AND ITS SYNTHETIC APPLICATION"TETRAHEDRON LETTERS. 42. 4861-4863 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 淵上 寿雄: "メディエーター(電極触媒)を利用する有機電解合成"触媒. 44・3(印刷中). (2002)

    • Related Report
      2001 Annual Research Report
  • [Publications] TOSHIO FUCHIGAMI: "ORGANIC ELECTROCHEMISTRY. 4TH EDITION"MARCEL DEKKER. 15 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Hideki Ishii: "Highly Selective Anodic Monofluorination of 4-Arylthio-1,3-dioxolan-2-ones : A Marked Solvent Effect on Product Selectivity"Chemical Communications. 1617-1618 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Hideki Ishii: "Highly Selective Electrolytic Fluorination of Dimethoxyeshane, Its Homologues, and Crown Ethers"Tetrahedron. 56. 8877-8881 (2000)

    • Related Report
      2000 Annual Research Report
  • [Publications] Mohamed R.Shaaban: "Marked Solvent Effects on Regioselective Anodic Monofluorination of 4-Oxo-2-Pyrimidyl Sulfides"Journal of Organic Chemistry. 65・25. 8685-8689 (2000)

    • Related Report
      2000 Annual Research Report

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Published: 2000-04-01   Modified: 2016-04-21  

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