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Organic Synthesis Using Various Valences of Iodine Reagents

Research Project

Project/Area Number 25288047
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypePartial Multi-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionOsaka University

Principal Investigator

Minakata Satoshi  大阪大学, 工学(系)研究科(研究院), 教授 (90273599)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥18,720,000 (Direct Cost: ¥14,400,000、Indirect Cost: ¥4,320,000)
Fiscal Year 2015: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2014: ¥4,030,000 (Direct Cost: ¥3,100,000、Indirect Cost: ¥930,000)
Fiscal Year 2013: ¥10,660,000 (Direct Cost: ¥8,200,000、Indirect Cost: ¥2,460,000)
Keywordsヨウ素 / 超原子価ヨウ素 / 触媒反応 / アミノ化 / アミノ化反応 / 脱炭酸 / 酸化反応 / ハロゲン結合 / 不斉合成
Outline of Final Research Achievements

This research project was carried out for the development of novel iodine reagents, especially iodine(I), (III), and (V) compounds, and their use in organic synthesis. The synthesis of iodine(I) reagents, which has an unique Lewis acidity, and its application to organic reactions were achieved. In addition, novel iodine(III) reagents containing nitrogen functional groups as a ligand were successfully synthesized, and they could be applied to amination reactions. The new type of amination reaction using iodine(V) reagents was also developed.

Report

(4 results)
  • 2015 Annual Research Report   Final Research Report ( PDF )
  • 2014 Annual Research Report
  • 2013 Annual Research Report
  • Research Products

    (31 results)

All 2016 2015 2014 2013

All Journal Article (15 results) (of which Peer Reviewed: 15 results,  Acknowledgement Compliant: 6 results) Presentation (16 results) (of which Int'l Joint Research: 4 results,  Invited: 3 results)

  • [Journal Article] Synthesis and Structure of Hypervalent Iodine(III) Reagents Containing Phthalimidate and Application to Oxidative Amination Reactions2015

    • Author(s)
      Kensuke Kiyokawa, Tomoki Kosaka, Takumi Kojima, and Satoshi Minakata
    • Journal Title

      Angew. Chem., Int. Ed.

      Volume: 54 Issue: 46 Pages: 13719-13723

    • DOI

      10.1002/anie.201506805

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Iodine-Catalyzed Decarboxylative Amidation of β,γ-Unsaturated Carboxylic Acids with Chloramine Salts Leading to Allylic Amides2015

    • Author(s)
      Kensuke Kiyokawa, Takumi Kojima, Yusuke Hishikawa, and Satoshi Minakata
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 44 Pages: 15548-15552

    • DOI

      10.1002/chem.201503298

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A facile synthesis of functionalized 7,8-diaza[5]helicenes through an oxidative ring-closure of 1,1’-binaphthalene-2,2’-diamines (BINAMs)2015

    • Author(s)
      Youhei Takeda, Masato Okazaki, Yoshiaki Maruoka, and Satoshi Minakata
    • Journal Title

      Beilstein J. Org. Chem.

      Volume: 11 Pages: 9-15

    • DOI

      10.3762/bjoc.11.2

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 2-Halogenoimidazolium Salt Catalyzed Aza-Diels-Alder Reaction through Halogen-Bond Formation2015

    • Author(s)
      Youhei Takeda, Daichi Hisakuni, Chun-Hsuan Lin, and Satoshi Minakata
    • Journal Title

      Org. Lett.

      Volume: 17 Issue: 2 Pages: 318-321

    • DOI

      10.1021/ol503426f

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Revisiting Phosphorus Analogues of Phthalimides and Naphthalimides: Syntheses and Comparative Studies2015

    • Author(s)
      Youhei Takeda, Takuya Nishida, Kota Hatanaka, and Satoshi Minakata
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 4 Pages: 1666-1672

    • DOI

      10.1002/chem.201405494

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Straightforward Synthesis of 1,2-Dicyanoalkanes from Nitroalkenes and Silyl Cyanide Mediated by Tetrabutylammonium Fluoride2015

    • Author(s)
      Kensuke Kiyokawa, Takaya Nagata, Junpei Hayakawa, and Satoshi Minakata
    • Journal Title

      Chem. Eur. J.

      Volume: 21 Issue: 3 Pages: 1280-1285

    • DOI

      10.1002/chem.201404780

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Hypervalent Iodine(III)-Mediated Oxidative Decarboxylation of β,γ-Unsaturated Carboxylic Acids2014

    • Author(s)
      Kensuke Kiyokawa, Shunsuke Yahata, Takumi Kojima, and Satoshi Minakata
    • Journal Title

      Org. Lett.

      Volume: 16 Issue: 17 Pages: 4646-4649

    • DOI

      10.1021/ol5022433

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Oxidative Skeletal Rearrangement of 1,1’-Binaphthalene-2,2’-Diamines (BINAMs) via C-C Bond Cleavage and Nitrogen Migration: A Versatile Synthesis of U-Shaped Azaacenes2014

    • Author(s)
      Youhei Takeda, Masato Okazaki, and Satoshi Minakata
    • Journal Title

      Chem. Commun.

      Volume: 50 Issue: 71 Pages: 10291-10294

    • DOI

      10.1039/c4cc04911j

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] 2,6-Diphospha-s-indacene-1,3,5,7(2H,6H)-tetraone: A Phosphorus Analogue of Aromatic Diimides with the Minimal Core Exhibiting High Electron-accepting Ability2014

    • Author(s)
      Youhei Takeda, Takuya Nishida, and Satoshi Minakata
    • Journal Title

      Chem. Eur. J.

      Volume: 20 Issue: 33 Pages: 10266-10270

    • DOI

      10.1002/chem.201403735

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Pd/NHC-Catalyzed Enantiospecific and Regioselective Suzuki-Miyaura Arylation of 2-Arylaziridines: Synthesis of Enantioenriched 2-Arylphenethylamine Derivatives2014

    • Author(s)
      Youhei Takeda, Yuki Ikeda, Akinobu Kuroda, Shino Tanaka, and Satoshi Minakata
    • Journal Title

      J. Am. Chem. Soc.

      Volume: 136 Issue: 24 Pages: 8544-8547

    • DOI

      10.1021/ja5039616

    • Related Report
      2014 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Oxidative Dimerization of (Hetero)aromatic Amines Utilizing t‐BuOI Leading to (Hetero)aromatic Azo Compounds: Scope and Mechanistic Studies2013

    • Author(s)
      Satoshi Minakata
    • Journal Title

      J. Org. Chem.

      Volume: 78 Issue: 23 Pages: 12090-12105

    • DOI

      10.1021/jo402120w

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Metal-Free Aziridination of Styrene Derivatives with Iminoiodinane Catalyzed by a Combination of Iodine and Ammonium Iodide2013

    • Author(s)
      Satoshi Minakata
    • Journal Title

      Org. Lett.

      Volume: 15 Issue: 18 Pages: 4858-4861

    • DOI

      10.1021/ol402276f

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] PCy_3-Catalyzed Ring-Expansion of Aziridinofullerenes with CO_2 and Aryl Isocyanates : Evidence for a Two-Conseutive Nucleophilic Substitution Pathway on the Fullerene Cage2013

    • Author(s)
      Satoshi Minakata
    • Journal Title

      Chem. Eur. J.

      Volume: 19 Issue: 40 Pages: 13479-13483

    • DOI

      10.1002/chem.201301617

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Hypervalent Iodine(III)-Induced Oxidative [4+2] Annulation of o-Phenylenediamines and Electron-Deficient Alkynes : Direct Synthesis of Quinoxalines from Alkyne Substrates under Metal-Free Conditions2013

    • Author(s)
      Satoshi Minakata
    • Journal Title

      Chem. Commun.

      Volume: 49 Issue: 81 Pages: 9266-9268

    • DOI

      10.1039/c3cc45469j

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Journal Article] A Practical Synthesis of Azobenzenes through Oxidative Dimerization of Aromatic Amines Using tert-Butyl Hypoiodite2013

    • Author(s)
      Satoshi Minakata
    • Journal Title

      Synthesis

      Volume: 45 Issue: 08 Pages: 1029-1033

    • DOI

      10.1055/s-0032-1318388

    • Related Report
      2013 Annual Research Report
    • Peer Reviewed
  • [Presentation] ヨウ素触媒存在下、クロラミン-Nsを窒素源とするオレフィン類のビシナルジアミノ化2016

    • Author(s)
      平山 新,三輪勇人,南方聖司
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学、京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヨウ素酸とN-ヒドロキシフタルイミドを活用した第三級炭素のリッター型C-Hアミノ化2016

    • Author(s)
      竹本憲太,伊東 亮,清川謙介,南方聖司
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学、京田辺キャンパス
    • Year and Date
      2016-03-24
    • Related Report
      2015 Annual Research Report
  • [Presentation] Iodine-catalyzed diamination of olefins using haloamide salt2015

    • Author(s)
      Satoshi Minakata, Arata Hirayama, Shino Tanaka
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Synthesis and structure of hypervalent iodine(III) reagent containing phthalimidate and its application to oxidative amination reaction2015

    • Author(s)
      Kensuke Kiyokawa, Tomoki Kosaka, Satoshi Minakata
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Hypervalent iodine(III)-mediated decarboxylative functionalization of β,γ-unsaturated carboxylic acids2015

    • Author(s)
      Takumi Kojima, Kensuke Kiyokawa, Satoshi Minakata
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Ritter-type C–H amination using N-hydroxyphthalimide and iodic acid2015

    • Author(s)
      Kenta Takemoto, Kensuke Kiyokawa, Satoshi Minakata
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu, Hawaii
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ヨウ素酸とN-ヒドロキシフタルイミドを用いた第三級C-H結合のリッター型アミノ化2015

    • Author(s)
      竹本憲太, 清川謙介, 南方聖司
    • Organizer
      第18回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学、千葉県千葉市
    • Year and Date
      2015-09-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヨウ素触媒を用いたクロラミン塩を窒素源とするβ,γ-不飽和カルボン酸の脱炭酸アミノ化反応2015

    • Author(s)
      小嶋匠実・菱川友輔・清川謙介・ 南方聖司
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 理工学部船橋キャンパス 千葉
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] フタルイミデートを有する超原子価ヨウ素試薬の合成とイミド化反応への活用2015

    • Author(s)
      小坂知輝・清川謙介・南方聖司
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学 理工学部船橋キャンパス 千葉
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 超原子価ヨウ素試薬を活用するβ,γ-不飽和カルボン酸の脱炭酸酸素官能化2014

    • Author(s)
      矢羽田駿介,清川謙介, 南方聖司
    • Organizer
      第41回有機典型元素化学討論会
    • Place of Presentation
      宇部市文化会館文化ホール 宇部
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Annual Research Report
  • [Presentation] 超原子価ヨウ素試薬を用いるβ,γ-不飽和カルボン酸の脱炭酸イミド化反応2014

    • Author(s)
      小嶋匠実,清川謙介,南方聖司
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀 東京
    • Year and Date
      2014-10-14 – 2014-10-16
    • Related Report
      2014 Annual Research Report
  • [Presentation] 超原子価ヨウ素試薬を用いるβ,γ-不飽和カルボン酸の脱炭酸イミド化反応2014

    • Author(s)
      小嶋匠実,清川謙介,南方聖司
    • Organizer
      第17回ヨウ素学会シンポジウム
    • Place of Presentation
      千葉大学けやき会館 千葉
    • Year and Date
      2014-09-19
    • Related Report
      2014 Annual Research Report
  • [Presentation] Hypervalent Iodine(III)-Mediated Oxidative Decarbonylation of β,γ-Unsaturated Carboxylic Acids2014

    • Author(s)
      Kensuke Kiyokawa,Shunsuke Yahata,Takumi Kojima, Satoshi Minakata
    • Organizer
      4th International Conference on Hypervalent Iodine Chemistry
    • Place of Presentation
      Hilton Narita, Chiba
    • Year and Date
      2014-07-02 – 2014-07-05
    • Related Report
      2014 Annual Research Report
  • [Presentation] 超原子価ヨウ素試剤を用いるアリルカルボン酸の脱炭酸アセトキシ化反2014

    • Author(s)
      南方聖司
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] ヨウ素/アンモニウム塩触媒を活用したイミノヨージナンを窒素源とするアジリジン合成2013

    • Author(s)
      南方聖司
    • Organizer
      ヨウ素学会
    • Place of Presentation
      千葉大学
    • Related Report
      2013 Annual Research Report
    • Invited
  • [Presentation] ヨードベンゼンジアセタートを活用するo-フェニレンジアミンと電子不足アルキンからのキノキサリン誘導体の合2013

    • Author(s)
      南方聖司
    • Organizer
      第3回CSJ化学フェスタ
    • Place of Presentation
      船堀タワーホール(東京)
    • Related Report
      2013 Annual Research Report
    • Invited

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Published: 2013-05-21   Modified: 2019-07-29  

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