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One-pot preparation of heterocycles with diaryliodoniums under transition-metal-free conditions

Research Project

Project/Area Number 15K05418
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Organic chemistry
Research InstitutionChiba University

Principal Investigator

Togo Hideo  千葉大学, 大学院理学研究院, 教授 (60217461)

Project Period (FY) 2015-04-01 – 2018-03-31
Project Status Completed (Fiscal Year 2017)
Budget Amount *help
¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000)
Fiscal Year 2017: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2016: ¥1,170,000 (Direct Cost: ¥900,000、Indirect Cost: ¥270,000)
Fiscal Year 2015: ¥2,600,000 (Direct Cost: ¥2,000,000、Indirect Cost: ¥600,000)
Keywordsジアリールヨードニウム / クマリン / キノリン / クロメン / 1工程合成反応 / 環化反応 / ジアリールヨードニウム塩 / ラジカル反応 / O-アリール化反応 / 3-アリールプロピン酸 / N-(プロパルギル)トシルアミド / キノリン誘導体 / ヨード環化反応 / NIS / N-アリール化反応 / ヨウ素 / ワンポット合成
Outline of Final Research Achievements

Treatment of 3-aryl-2-propyn-1-ols with diaryliodonium salts, followed by the reaction with NIS and BF3 gave 4-aryl-3-iodochromenes, treatment of N-tosyl 3-aryl-2-propynyl-1-amines with diaryliodonium salts, followed by the reaction with NIS and BF3 gave 4-aryl-3-iodoquinolines, and treatment of 3-aryl-2-propynoic acids with diaryliodonium salts, followed by the reaction with TBAB and Na2S2O8 gave 4-aryl-3-bromocoumarins in good yields, respectively. Those preparation methods are one-pot reactions of chromene, quinoline, and coumarin units. Moreover, those obtained 4-aryl-3-iodochromenes, 4-aryl-3-iodoquinolines, and 4-aryl-3-bromocoumarins were transformed to various 4-arylcoumarine derivatives and 4-arylquinoline derivatives by their oxidation, reduction, and coupling reaction with Pd complex.

Report

(4 results)
  • 2017 Annual Research Report   Final Research Report ( PDF )
  • 2016 Research-status Report
  • 2015 Research-status Report
  • Research Products

    (34 results)

All 2018 2017 2016 2015

All Journal Article (14 results) (of which Peer Reviewed: 14 results,  Open Access: 10 results,  Acknowledgement Compliant: 9 results) Presentation (15 results) (of which Int'l Joint Research: 2 results,  Invited: 2 results) Book (3 results) Patent(Industrial Property Rights) (2 results)

  • [Journal Article] One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and Na2S2O82018

    • Author(s)
      Sasaki Teppei、Moriyama Katsuhiko、Togo Hideo
    • Journal Title

      Beilstein Journal of Organic Chemistry

      Volume: 14 Pages: 345-353

    • DOI

      10.3762/bjoc.14.22

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Introduction of Quinolines and Isoquinolines onto Nonactivated α-C?H Bond of Tertiary Amides through a Radical Pathway2017

    • Author(s)
      Okugawa Naoki、Moriyama Katsuhiko、Togo Hideo
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 1 Pages: 170-178

    • DOI

      10.1021/acs.joc.6b02303

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] One-Pot Preparation of C1-Homologated Aliphatic Nitriles from Aldehydes through a Wittig Reaction under Metal-Cyanide-Free Conditions2017

    • Author(s)
      Ezawa Masatoshi、Togo Hideo
    • Journal Title

      European Journal of Organic Chemsiry

      Volume: 2017 Issue: 16 Pages: 2379-2384

    • DOI

      10.1002/ejoc.201700277

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Preparation of 3-Iodoquinolines from N-Tosyl-2-propynylamines with Diaryliodonium Triflate and N-Iodosuccinimide2017

    • Author(s)
      Sasaki Teppei、Moriyama Katsuhiko、Togo Hideo
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 82 Issue: 22 Pages: 11727-11734

    • DOI

      10.1021/acs.joc.7b01433

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] Hydroxymethylation of Quinolines with Na2S2O8 by a Radical Pathway2017

    • Author(s)
      Zhou Luan、Okugawa Naoki、Togo Hideo
    • Journal Title

      European Journal of Organic Chemsiry

      Volume: 2017 Issue: 41 Pages: 6239-6245

    • DOI

      10.1002/ejoc.201701321

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed / Open Access
  • [Journal Article] One-pot transformation of Aliphatic Carboxylic Acids into N-Alkylsuccinimides with NIS and NCS/NaI2016

    • Author(s)
      Yuhta Nakai, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 19 Issue: 4 Pages: 768-772

    • DOI

      10.1002/ejoc.201501315

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Direct Transformation of Ethylarenes into Primary Aromatic Amides with N‐Bromosuccinimide and I2-Aqueous NH32016

    • Author(s)
      Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 4 Pages: 784-787

    • DOI

      10.1021/acs.orglett.6b00048

    • Related Report
      2016 Research-status Report 2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Direct Preparation of 3-Iodochromenes from 3-Aryl- and 3-Alkyl-2-propyn-1-ols with Diaryliodonium Salts and NIS2016

    • Author(s)
      Teppei Sasaki, Kotaro Miyagi, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 5 Pages: 944-947

    • DOI

      10.1021/acs.orglett.5b03651

    • Related Report
      2016 Research-status Report 2015 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Preparation of 5-Aryl-2-Alkyltetrazoles with Aromatic Aldehydes, Alkylhydrazine, Di-t-butyl Azodicarboxylate, and [bis(trifluoroacetoxy)iodo]benzene2016

    • Author(s)
      Tarou Imai, Ryo Harigae, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      The Journal of Organic Chemistry

      Volume: 81 Issue: 9 Pages: 3975-3980

    • DOI

      10.1021/acs.joc.6b00606

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Synthetic Utility of Iodic Acid in the Oxidation of Benzylic Alcohols to Aromatic Aldehydes and Ketones2016

    • Author(s)
      Sho Imai, Hideo Togo
    • Journal Title

      Tetrahedron

      Volume: 72 Issue: 44 Pages: 6948-6954

    • DOI

      10.1016/j.tet.2016.09.019

    • Related Report
      2016 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Facile One-Pot Transformation of Arenes into Aromatic Nitriles Under Metal Cyanide-Free Conditions2015

    • Author(s)
      Toshiyuki Tamura, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 18 Pages: 2023-2029

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A One-Pot, Transition-Metal-Free Procedure for C-O, C-S, and C-N Bond Formation at Benzylic Position of Methylarenes2015

    • Author(s)
      Hiroyuki Shimojo, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      Synthesis

      Volume: 47 Pages: 1280-1290

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] One-pot Preparation of 2,5-Disubstituted and 2,4,5-Trisubstituted Oxazoles from Aromatic Ketones with Molecular Iodine, Oxone, and Trifluoromethanesulfonic Acid in Nitriles2015

    • Author(s)
      Sho Imai, Hiroki Kikui, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      Tetrahedron

      Volume: 71 Pages: 5267-5274

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Introduction of Ether Groups onto Electron-deficient Nitrogen-containing Heteroaromatics Using Radical Chemistry under Transition-metal-free Conditions2015

    • Author(s)
      Naoyuki Okugawa, Katsuhiko Moriyama, Hideo Togo
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 18 Pages: 4973-4981

    • Related Report
      2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 超原子価ヨウ素を用いたクマリン誘導体のワンポット合成反応2018

    • Author(s)
      佐々木哲平、東郷秀雄
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 単体ヨウ素及び超原子価ヨウ素を用いた有機反応の開発2017

    • Author(s)
      東郷秀雄
    • Organizer
      第17回ヨウ素学会シンポジウム
    • Related Report
      2017 Annual Research Report
    • Invited
  • [Presentation] 超原子価ヨウ素によるプロパルギルアミン類からキノリン誘導体のワンポット合成反応2017

    • Author(s)
      佐々木哲平、森山克彦、東郷秀雄
    • Organizer
      第17回ヨウ素学会シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] ジアリールヨードニウム塩を用いたキノリン誘導体のワンポット合成反応2017

    • Author(s)
      佐々木哲平、森山克彦、東郷秀雄
    • Organizer
      日本プロセス化学会シンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] 超原子価ヨウ素を用いたキノリン誘導体のワンポット合成反応2017

    • Author(s)
      佐々木哲平、森山克彦、東郷秀雄
    • Organizer
      日本化学会第97春季年会
    • Related Report
      2017 Annual Research Report 2016 Research-status Report
  • [Presentation] 臭素とヨウ素の特性を活かした酸化的反応開発2016

    • Author(s)
      東郷秀雄
    • Organizer
      2016ハロゲン利用ミニシンポジウム
    • Place of Presentation
      佐賀大学(佐賀県佐賀市)
    • Year and Date
      2016-11-25
    • Related Report
      2016 Research-status Report
    • Invited
  • [Presentation] ジアリールヨードニウム塩を用いたプロパルギルアルコールからベンゾピラン誘導体の遷移金属フリー・ワンポット合成反応2016

    • Author(s)
      佐々木哲平、森山克彦、東郷秀雄
    • Organizer
      第19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
      2016-09-16
    • Related Report
      2016 Research-status Report
  • [Presentation] 超原子価ヨウ素を用いたアルデヒドからテトラゾール誘導体へのワンポット変換反応2016

    • Author(s)
      今井太郎、森山克彦、東郷秀雄
    • Organizer
      第19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
      2016-09-16
    • Related Report
      2016 Research-status Report
  • [Presentation] ヨウ素酸によるアルコールのアルデヒドやケトンへの酸化反応2016

    • Author(s)
      今井 奨、東郷秀雄
    • Organizer
      第19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
      2016-09-16
    • Related Report
      2016 Research-status Report
  • [Presentation] ラジカル反応を経由した電子欠損型含窒素芳香環類への第三級アミド鎖の導入反応の開発2016

    • Author(s)
      奥川直紀、東郷秀雄
    • Organizer
      2016日本プロセス化学会サマーシンポジウム
    • Place of Presentation
      名古屋国際会議場(愛知県名古屋市)
    • Year and Date
      2016-07-27
    • Related Report
      2016 Research-status Report
  • [Presentation] C-C結合開裂を経たエチルアレーンの芳香族第一級アミドへの金属を用いないワンポット変換反応2016

    • Author(s)
      下川翔平、森山克彦、東郷秀雄
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学( 京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] ジアリールヨードニウム塩とNISを用いたプロパルギルアルコールからベンゾピランへの遷移金属フリーなOne-pot反応2016

    • Author(s)
      佐々木哲平、森山克彦、東郷秀雄
    • Organizer
      日本化学会第96春季年会
    • Place of Presentation
      同志社大学( 京都府京田辺市)
    • Year and Date
      2016-03-24
    • Related Report
      2015 Research-status Report
  • [Presentation] One-pot Synthesis of Oxazoles from Ketones Using Molecular Iodine2015

    • Author(s)
      今井 奨、森山克彦、東郷秀雄
    • Organizer
      第17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 Research-status Report
  • [Presentation] One-pot Transformation of Aliphatic Carboxylic Acids into N-Alkylsuccinimides2015

    • Author(s)
      Yuhta Nakai, Katsuhiko Moriyama, Hideo Togo
    • Organizer
      The 3rd International Symposium on Process Chemistry
    • Place of Presentation
      京都国際会議場( 京都府京都市)
    • Year and Date
      2015-07-13
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Presentation] One-pot Transformation of Arenes into Aromatic Nitriles under Metal-Cyanide-Free Conditions2015

    • Author(s)
      Toshiyuki Tamura, Katsuhiko Moriyama, Hideo Togo
    • Organizer
      The 3rd International Symposium on Process Chemistry
    • Place of Presentation
      京都国際会議場( 京都府京都市)
    • Year and Date
      2015-07-13
    • Related Report
      2015 Research-status Report
    • Int'l Joint Research
  • [Book] 有機合成化学---最先端の研究例から学ぶ合成戦略と反応機構---2016

    • Author(s)
      東郷秀雄
    • Total Pages
      399
    • Publisher
      講談社
    • Related Report
      2016 Research-status Report
  • [Book] 有機合成化学2016

    • Author(s)
      東郷秀雄
    • Total Pages
      432
    • Publisher
      講談社
    • Related Report
      2015 Research-status Report
  • [Book] 有機合成のための有機フリーラジカル反応2015

    • Author(s)
      東郷秀雄
    • Total Pages
      314
    • Publisher
      丸善
    • Related Report
      2015 Research-status Report
  • [Patent(Industrial Property Rights)] カルボニル化合物の製造方法2016

    • Inventor(s)
      東郷秀雄、今井 奨、宮本充彦
    • Industrial Property Rights Holder
      東郷秀雄、今井 奨、宮本充彦
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2016-134945
    • Filing Date
      2016-07-07
    • Related Report
      2016 Research-status Report
  • [Patent(Industrial Property Rights)] N-アルキルイミド化合物の製造法2015

    • Inventor(s)
      東郷秀雄、仲井優太、森山克彦、宮本充彦
    • Industrial Property Rights Holder
      東郷秀雄、仲井優太、森山克彦、宮本充彦
    • Industrial Property Rights Type
      特許
    • Industrial Property Number
      2015-172647
    • Filing Date
      2015-09-02
    • Related Report
      2015 Research-status Report

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Published: 2015-04-16   Modified: 2019-03-29  

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