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STUDY OF POLYMER-SUPPORTED DESS-MARTIN HYPERVALENT IODINE REAGENT

Research Project

Project/Area Number 13554028
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section展開研究
Research Field 物質変換
Research InstitutionCHIBA UNIVERSITY

Principal Investigator

TOGO Hideo  Chiba University, Department of Chemistry Faculty of Science, Associate Professor, 理学部, 助教授 (60217461)

Co-Investigator(Kenkyū-buntansha) KAIHO Tasuo  Mitsui Chemicals Co., Material Chemicals Lab., Chief Researcher, 有機機能材料研究所, 主席研究員
YAMAGUCHI Kentaro  Chiba University, Chemical Analysis Center, Associate Professor, 分析センター, 助教授 (50159208)
Project Period (FY) 2001 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥5,900,000 (Direct Cost: ¥5,900,000)
Fiscal Year 2003: ¥1,500,000 (Direct Cost: ¥1,500,000)
Fiscal Year 2002: ¥1,300,000 (Direct Cost: ¥1,300,000)
Fiscal Year 2001: ¥3,100,000 (Direct Cost: ¥3,100,000)
KeywordsAlcohol / Ketone / Aldehyde / Environmental Benign / Polymer-supported Hypervalent Iodine / リサイクル / カルボン酸 / 高分子型超原子価ヨウ素酸化
Research Abstract

Primary and secondary alcohols were successfully oxidized to the corresponding aldehydes and ketones at room temperature in good yields, respectively, with poly[4-(diacetoxyiodo)styrene] (PSDIB) in the presence of TEMPO (cat.) in acetone, as an environmentally friendly method. Here, polymer-supported hypervapent iodine was quantitatively recovered by simple filtration from the reaction mixture, and PSDIB was regenerated by treatment with peracetic acid and reused successfully. The previous methods such as Swern oxidation and Dess-Martin oxidation may be substituted by the present method, since the present oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones, respectively, is effective and secure as an operationally simple and environmentally benign method, and can be used for the synthesis of pharmaceutical and agrochemical substances

Report

(4 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • 2001 Annual Research Report
  • Research Products

    (66 results)

All Other

All Publications (66 results)

  • [Publications] S.Abe, K.Sakuratani, H.Togo: "Novel Preparation and Reactivity of Poly[4-hydroxy-(tosyloxy)iodo]styrene"Synlett. 22-24 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] A.Ryokawa, H.Togo: "Synthetic Use of 1,1,2,2-Tetraphenyldisilane for the Preparation of Biaryls Through the Intramolecular Free Radical ipso-Substitution of N-(2-"Tetrahedron. 57. 5915-5921 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] "Synthetic Use of Poly[4-hydroxy(tosyloxy)iodo]styrenes"J.Org.Chem.. 66. 6174-6177 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Katohgi, H.Togo: "Oxidatively Sonochemical Dealkylation of Various N-Alkylsulfonamides to Free Sulfonamides and Aldehydes"Tetrahedron. 57. 7481-7486 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo, M.Katohgi: "Synthetic Uses of Organohypervalent Iodine Compounds Through Radical Pathways"Synlett. 565-581 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo, M.Sugi, K.Toyama: "1,1,2,2-Tetraphenyldisilane (TPDS) as a New Diversified Radical Reagent"Comptes Rendus Serie IIc. 539-546 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Sugi, H.Togo: "Environmentally Friendly TPDS-Mediated Free Radical Ring Expansion of α-Haloalkyl Cyclic β-Keto Esters"Tetrahedron. 58. 3171-3175 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Nabana, H.Togo: "Reactivity of Novel [Hydroxy(tosyloxy)iodo]arenes and [Hydroxy(phosphoryloxy)iodo]arenes for α-Tosyloxylation and α-phosphoryloxylation of Ketones"J.Org.Chem.. 67. 4362-4365 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sakuratani, H.Togo: "Polymer-Supported Hypervalent Iodine Reagents"Synlett. 1966-1975 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 東郷秀雄: "環境調和型化学変換試剤:高分子リサイクル型超原子価ヨウ素酸化剤の開発と展開"エコインダストリー(Eco Industry). 7. 5-18 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 東郷秀雄, 櫻谷憲司: "高性能ポリマー型酸化試剤"化学と工業(日本化学会誌). 55. 1018-1020 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sakuratani, H.Togo: "Environmentaly Friendly TEMPO-mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"Synthesis. 22-23 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 東郷秀雄: "環境に優しいラジカル反応試剤TPDSを用いた有機反応"ファインケミカル. 44-53 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sakuratani, Hideo Togo: "Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxide with Polymer-supported Hypervalent Iodine Reagents."ARKIVOC. 11-20 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Misu, H.Togo: "Novel Preparation of 2,1-Benzothiazine Derivatives from Sulfonamides with [Hydroxy(tosyloxy)iodo]arenes"Org.Biomol.Chem.. 1. 1342-1346 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sakuratani, H.Togo: "Environmentaly Friendly TEMPO-mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"Synthesis. 21-23 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo, T.Hirai: "Environmentally-Friendly Wohl-Ziegler Bromination : Ionic-Liquid Reaction and Solvent-Free Reaction"Synlett. 702-704 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Ueno, T.Nabana, H.Togo: "Novel Oxidative a-Tosyloxylation of Alcohols with Iodosylbenzene and p-Toluenesulfonic Acid, and Its Synthetic Application for the Direct"J.Org.Chem.. 68. 6424-6425 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Sugi, D.Sakuma, H.Togo: "Zinc- and Indium-mediated Ring-Expansion Reaction of a-Halomethyl Cyclic b-Keto Esters in Aqueous Alcohol"J.Org.Chem.. 68. 7629-7633 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 東郷秀雄: "有機フリーラジカルの化学"講談社サイエンティフィク. 187 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 東郷秀雄: "有機反応のしくみと考え方"講談社サイエンティフィク. 273 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Hideo Togo: "Advanced Free Radical Reactions for Organic Synthesis"Elsevier Science. 258 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] 東郷秀雄: "実験化学講座 第5版,19巻 2章"ラジカル反応""丸善. 43 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Abe, K.Sakuratani, H.Togo: "Novel Preparation and Reactivity of Poly[4-hydroxy-(tosyloxy)iodo]-styrene"Synlett. 22-24 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] A.Ryokawa, H.Togo: "Synthetic Use of 1,1,2,2-Tetraphenyldisilane for the Preparation of Biaryls Through the Intramolecular Free Radical ipso-Substitution of N-(2-Bromoaryl)arenesulfonamides"Tetrahedron. 57. 5915-5921 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] S.Abe, K.Sakuratani, H.Togo: "Synthetic Use of Poly[4-hydroxy(tosyloxy)iodo]styrenes"J.Org.Chem.. 66. 6174-6177 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Katohgi, H.Togo: "Oxidatively Sonochemical Dealkylation of Various N-Alkylsulfonamides to Free Sulfonamides and Aldehydes"Tetrahedron. 57. 7481-7486 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo, M.Katohgi: "Synthetic Uses of Organohypervalent Iodine Compounds Through Radical Pathways"Synlett. 565-581 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo, M.Sugi, K.Toyama: "1,1,2,2-Tetraphenyldisilane (TPDS) as a New Diversified Radical Reagent"Compt.Rend.Serie IIc. 539-546 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Sugi, H.Togo: "Environmentally Friendly TPDS-Mediated Free Radical Ring Expansion of a-Haloalkyl Cyclic b-Keto Esters"Tetrahedron. 58. 3171-3175 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] T.Nabana, H.Togo: "Reactivity of Novel [Hydroxy(tosyloxy)iodo]arenes and [Hydroxy(phosphoryloxy)iodo]arenes for a-Tosyloxylation and a-phosphoryloxylation of Ketones"J.Org.Chem.. 67. 4362-4365 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sakuratani, H.Togo: "Environmentally Friendly TEMPO-mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"Synthesis. 22-23 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo, K.Sakuratani: "Polymer-Supported Hypervalent Iodine Reagents"Synlett. 1966-1975 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo: "Environmentally Benign Reagents : Study of Polymer-supported Recyclable Hypervalent Iodine Reagents (Japanese)"Eco Industry. 7. 5-18 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo: "Organic Free Radical Reactions with TPDS (Japanese)"Finechemicals. 44-53 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sakuratani, Hideo Togo: "Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxide with Polymer-supported Hypervalent Iodine Reagents"ARKIVOC. 11-20 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] Y.Misu, H.Togo: "Novel Preparation of 2,1-Benzothiazine Derivatives from Sulfonamides with [Hydroxy(tosyloxy)iodo]arenes"Org.Biomol.Chem.. 1. 1342-1346 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sakuratani, H.Togo: "Environmentally Friendly TEMPO-mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"Synthesis. 21-23 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo, T.Hirai: "Environmentally-Friendly Wohl-Ziegler Bromination : Ionic-Liquid Reaction and Solvent-Free Reaction"Synlett. 702-704 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Ueno, T.Nabana, H.Togo: "Novel Oxidative a-Tosyloxylation of Alcohols with Iodosylbenzene and p-Toluenesulfonic Acid, and Its Synthetic Application for the Direct Preparation of Heteroaromatics"J.Org.Chem.. 68. 6424-6425 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Sugi, D.Sakuma, H.Togo: "Zinc-and Indium-mediated Ring-Expansion Reaction of a-halomethyl Cyclic b-Keto Esters in Aqueous Alcohol"J.Org.Chem.. 68. 7629-7633 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo: "Organic Free Radical Reactions (Japanese)"Kohdansha. 1-187 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo: "Mechanism of Organic Reactions"Kohdansha. 1-271 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo: "Radical Reactions in Organic Synthesis (Japanese) 19"Maruzen. (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Togo: "Advanced Free Radical Reactions for Organic Synthesis"Elsevier Science. 1-258 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] K.Sakuratani, H.Togo: "Preparation of 3,4-Dihydro-2,1-benzothiazine 2,2-Dioxide with Polymer-supported Hypervalent Iodine Reagents"ARKIVOC. 11-20 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Y.Misu, H.Togo: "Novel Preparation of 2,1-Benzothiazine Derivatives from Sulfonamides with [Hydroxy(tosyloxy)iodo]arenes"Org.Biomol.Chem.. 1. 1342-1346 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] K.Sakuratani, H.Togo: "Environmentaly Friendly TEMPO-mediated Oxidation of Alcohols with Poly[4-(diacetoxyiodo)styrene]"Synthesis. 21-23 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] H.Togo, T.Hirai: "Environmentally-Friendly Wohl-Ziegler Bromination : Ionic-Liquid Reaction and Solvent-Free Reaction"Synlett. 702-704 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Ueno, T.Nabana, H.Togo: "Novel Oxidative a-Tosyloxylation of Alcohols with Iodosylbenzene and p-Toluenesulfonic Acid, and Its Synthetic Application for the Direct Preparation of Heteroaromatics"J.Org.Chem.. 68. 6424-6425 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Sugi, D.Sakuma, H.Togo: "Zinc- and Indium-mediated Ring-Expansion Reaction of a-halomethyl Cyclic b-Keto Esters in Aqueous Alcohol"J.Org.Chem.. 68. 7629-7633 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] Hideo Togo: "Advanced Free Radical Reactions for Organic Synthesis"Elsevier Science. 258 (2004)

    • Related Report
      2003 Annual Research Report
  • [Publications] Masaaki Sugi, H.Togo: "Environmentally Friendly TPDS-Mediated Free Radical Ring Expansion of α-Haloalkyl Cyclic β-Keto Esters"Tetrahedron. 58. 3171-3175 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] T.Nabana, H.Togo: "Reactivity of Novel [Hydroxy(tosyloxy)iodo]arenes and [Hydroxy(phosphoryloxy)iodo]arenes for α-Tosyloxylation and α-phosphoryloxylation of Ketones"Journal of Organic Chemistry. 67. 4362-4365 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] H.Togo, K.Sakuratani: "Polymer-Supported Hypervalent Iodine Reagents"Synlett. 1966-1975 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 東郷秀雄: "環境調和型化学変換試剤:高分子リサイクル型超原子価ヨウ素酸化剤の開発と展開"エコインダストリー(Eco Inductry). 7. 5-18 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] 東郷秀雄, 櫻谷憲司: "高性能ポリマー型酸化試剤"化学と工業(日本化学会誌). 55. 1018-1020 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] K.Sakuratani, H.Togo: "Environmentaly Friendly TEMPO-mediated Oxidation of Alcohols with Poly [4-(diacetoxyiodo)styrene]"Synthesis. 21-23 (2003)

    • Related Report
      2002 Annual Research Report
  • [Publications] 東郷秀雄: "有機反応のしくみと考え方"講談社サイエンティフィク. 273 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] S.Abe, K.Sakuratani, H.Togo: "Novel Preparation and Reactivity of Poly[4-hydroxy(tosyloxy)iodo]styrene"Synlett. 22-24 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] A.Ryokawa, H.Togo: "Synthetic Use of 1,1,2,2-Tetraphenyldisilane for the Preparation of Biaryls Through the Intramolecular Free Radical ipso-Substitution"Tetrahedron. 57. 5915-5921 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] S.Abe, K.Sakuratani, H.Togo: "Synthetic Use of Poly[4-hydroxy(tosyloxy)iodo]styrenes"Journal of Organic Chemistry. 66. 6174-6177 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] M.Katohgi, H.Togo: "Oxidatively Sonochemical Dealkylation of Various N-Alkylsulfon-amides to Free Sulfonamides and Aldehydes"Tetrahedron. 57. 7481-7486 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] Hideo Togo, Masashi Katohgi: "Synthetic Uses of Organohypervalent Iodine Compounds Through Radical Pathways"Synlett. 565-581 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] H.Togo, M.Sugi, K.Toyama: "1,1,2,2-Tetraphenyldisilane(TPDS)as a New Diversified Radical Reagent"Comptes Rendus de L'Academie des Sciences Serie IIc. 539-546 (2001)

    • Related Report
      2001 Annual Research Report
  • [Publications] 東郷秀雄: "有機フリーラジカルの化学"講談社サイエンティフィク. 187 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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