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Development of a novel indium reducing catalytic system leading to a chemoselective reduction of carboxylic acids

Research Project

Project/Area Number 25410120
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionTokyo University of Science

Principal Investigator

SAKAI NORIO  東京理科大学, 理工学部, 准教授 (00328569)

Project Period (FY) 2013-04-01 – 2016-03-31
Project Status Completed (Fiscal Year 2015)
Budget Amount *help
¥5,200,000 (Direct Cost: ¥4,000,000、Indirect Cost: ¥1,200,000)
Fiscal Year 2015: ¥1,690,000 (Direct Cost: ¥1,300,000、Indirect Cost: ¥390,000)
Fiscal Year 2014: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000)
Fiscal Year 2013: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000)
Keywordsインジウム / ヒドロシラン / 化学選択性 / 還元 / 官能基変換 / 還元反応 / カルボン酸 / 単体硫黄 / チオエーテル / ガリウム / ハロゲン化アルキル / チオール
Outline of Final Research Achievements

It was found that when carboxylic acids were treated with indium bromide and 1,1,3,3-tetremethyldisiloxane (TMDS) in the presence of either halogen sources or mercaptans, the corresponding alkyl iodides, alkyl bromides and sulfides were obtained through a single-step transformation. Also, the combination of indium iodide and TMDS chemoselectively and directly reduced secondary amides to produce the corresponding secondary amines. Moreover, the combination of either In(OTf)3-TMDS or InI3-Et3SiH successively reduced nitrobenzenes to produce the corresponding azobenzenes and anilines, respectively.

Report

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

    (73 results)

All 2016 2015 2014 2013 Other

All Journal Article (23 results) (of which Peer Reviewed: 23 results,  Acknowledgement Compliant: 15 results) Presentation (48 results) (of which Int'l Joint Research: 5 results,  Invited: 1 results) Remarks (2 results)

  • [Journal Article] Reductive Amination/Cyclization of Keto Acids Using a Hydrosilane for Selective Production of Lactams versus Cyclic Amines by Switching of the Indium Catalyst2016

    • Author(s)
      Yohei Ogiwara, Takuya Uchiyama, Norio Sakai
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 55 Issue: 5 Pages: 1864-1867

    • DOI

      10.1002/anie.201509465

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium-Catalyzed Reductive Sulfidation of Esters by Using Thiols: An Approach to the Diverse Synthesis of Sulfides2016

    • Author(s)
      Takahiro Miyazaki, Shinsei Kasai, Yohei Ogiwara, Norio Sakai
    • Journal Title

      European Journal of Organic Chemistry

      Volume: 5 Issue: 5 Pages: 1043-1049

    • DOI

      10.1002/ejoc.201501559

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium-Catalyzed Direct Preparation of Dibenzyl Sulfides from Benzyl Alcohols and Elemental Sulfur with a Hydrosilane and Its Application to the Preparation of Dibenzyl Selenide2016

    • Author(s)
      Takahiro Miyazaki, Masahiro Katayama, Shunsuke Yoshimoto, Yohei Ogiwara, Norio Sakai
    • Journal Title

      Tetrahedron Letters

      Volume: 57 Issue: 6 Pages: 676-679

    • DOI

      10.1016/j.tetlet.2015.12.109

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Production of Quaternary α-Aminonitriles by Means of Indium-Catalyzed Three-Component Reaction of Alkynes, Amines and Trimethylsilyl Cyanide2016

    • Author(s)
      Yuta Hamachi, Moe Katano, Yohei Ogiwara, Norio Sakai
    • Journal Title

      Organic Letters

      Volume: 18 Issue: 7 Pages: 1634-1637

    • DOI

      10.1021/acs.orglett.6b00508

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper-Catalyzed Coupling Reaction of Aryl Boronic Acids with N,O-acetals Leading to α-Arylglycine Derivatives and Diarylmethylamine Derivatives2015

    • Author(s)
      Norio Sakai, Hiroaki Hori, Yoshihiro Yoshida, Takeo Konakahara, Yohei Ogiwara
    • Journal Title

      Tetrahedron

      Volume: 71 Issue: 29 Pages: 4722-4729

    • DOI

      10.1016/j.tet.2015.05.068

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Oxidative Nitrosation of Secondary Amines with Nitromethane Under Basic Conditions2015

    • Author(s)
      Norio Sakai, Minoru Sasaki, Yohei Ogiwara
    • Journal Title

      Chemical Communications

      Volume: 51 Issue: 58 Pages: 11638-11641

    • DOI

      10.1039/c5cc03675e

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Indium-Catalyzed Reduction of Nitrobenzenes with a Hydrosilane Leading to Anilines: Scope and Limitations2015

    • Author(s)
      Norio Sakai, Shun Asama, Takeo Konakahara, Yohei Ogiwara
    • Journal Title

      Synthesis

      Volume: 47 Issue: 20 Pages: 3179-3185

    • DOI

      10.1055/s-0034-1378850

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] One-Pot Synthesis of Tetralin Derivatives From 3-Benzoylpropionic Acids: Indium-Catalyzed Hydrosilylation of Ketones and Carboxylic Acids and Intramolecular Cyclization2015

    • Author(s)
      Norio Sakai, Taichi Kobayashi, Yohei Ogiwara
    • Journal Title

      Chemistry Letters

      Volume: 44 Issue: 11 Pages: 1503-1505

    • DOI

      10.1246/cl.150686

    • NAID

      130005108087

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium-Catalyzed Reduction of Secondary Amides with a Hydrosiloxane Leading to Secondary Amines2015

    • Author(s)
      Norio Sakai, Masashi Takeoka, Takayuki Kumaki, Hirotaka Asano, Takeo Konakahara, Yohei Ogiwara
    • Journal Title

      Tetrahedron Letters

      Volume: 56 Issue: 46 Pages: 6448-6451

    • DOI

      10.1016/j.tetlet.2015.09.148

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Oxidative Coupling of Terminal Alkynes with Aldehydes Leading to Alkynyl Ketones by Using an Indium(III) Bromide2015

    • Author(s)
      Yohei Ogiwara, Masahito Kubota, Kotaro Kurogi, Takeo Konakahara, Norio Sakai
    • Journal Title

      Chemistry - A European Journal

      Volume: 21 Issue: 51 Pages: 18598-18600

    • DOI

      10.1002/chem.201504255

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium(III)-Catalyzed Reductive Monoalkylation of Electron-Rich Benzenes with Aliphatic Carboxylic Acids Leading to Arylalkane Derivatives2015

    • Author(s)
      Toshimitsu Moriya, Kentaro Takayama, Takeo Konakahara, Yohei Ogiwara, Norio Sakai
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2015 Issue: 10 Pages: 2277-2281

    • DOI

      10.1002/ejoc.201500096

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium(III)-Catalyzed Knoevenagel Condensation of Aldehydes and Activated Methylenes Using Acetic Anhydride as a Promoter2015

    • Author(s)
      Yohei Ogiwara, Keita Takahashi, Takefumi Kitazawa, Norio Sakai
    • Journal Title

      JOURNAL OF ORGANIC CHEMISTRY

      Volume: 80 Issue: 6 Pages: 3101-3110

    • DOI

      10.1021/acs.joc.5b00011

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium-Catalyzed Reductive Sulfidation of Aromatic Carboxylic Acids and Aldehydes with Elemental Sulfur to Prepare Symmetrical Benzyl Sulfides2015

    • Author(s)
      Takahiro Miyazaki, Kota Nishino, Shunsuke Yoshimoto, Yohei Ogiwara, Norio Sakai
    • Journal Title

      EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

      Volume: 2015 Issue: 9 Pages: 1991-1994

    • DOI

      10.1002/ejoc.201403567

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Copper(II)-Catalyzed [4+1] Annulation of Propargylamines with N,O-Acetals: Entry to the Synthesis of Polysubstituted Pyrrole Derivatives2015

    • Author(s)
      Norio Sakai, Hiroaki Hori, Yohei Ogiwara
    • Journal Title

      EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

      Volume: 2015 Issue: 9 Pages: 1905-1909

    • DOI

      10.1002/ejoc.201500098

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] One-Pot Preparation of Alkyl Iodides from Esters by Indium-Catalyzed Reductive Cleavage of Carbon-Oxygen Bond2015

    • Author(s)
      Norio Sakai, Yohei Matsushita, Takeo Konakahara, Yohei Ogiwara, Keisuke Hirano
    • Journal Title

      Eur. J. Org. Chem.

      Volume: 2015 Issue: 7 Pages: 1591-1595

    • DOI

      10.1002/ejoc.201403539

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Gallium-Catalyzed Reductive Chlorination of Carboxylic Acids with Copper(II) Chloride2014

    • Author(s)
      Norio Sakai, Takumi Nakajima, Shinichiro Yoneda, Takeo Konakahara, and Yohei Ogiwara
    • Journal Title

      J. Org. Chem.

      Volume: 79 Issue: 21 Pages: 10619-10623

    • DOI

      10.1021/jo501912v

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Indium-Catalyzed Hydroamination/Hydrosilylation of Terminal Alkynes and Aromatic Amines through a One-Pot, Two-Step Protocol2014

    • Author(s)
      Norio Sakai, Nobuaki Takahashi, Yohei Ogiwara
    • Journal Title

      EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

      Volume: 2014 Issue: 23 Pages: 5078-5082

    • DOI

      10.1002/ejoc.201402544

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] N-Aminomethylation vs. C-Aminomethylation of Indole and Pyrrole with an N,O-Acetal Controlled by the Hardness of a Counter Ion of an Iminium Compound2014

    • Author(s)
      Norio Sakai, Hidetoshi Okano, Kazuyori Shimamura, Takeo Konakahara
    • Journal Title

      CHEMISTRY LETTERS

      Volume: 43 Issue: 4 Pages: 501-503

    • DOI

      10.1246/cl.131116

    • NAID

      130004868072

    • Related Report
      2014 Research-status Report
    • Peer Reviewed
  • [Journal Article] Indium(III)-Catalyzed One-Pot Synthesis of Alkyl Cyanides from Carboxylic Acids2013

    • Author(s)
      Toshimitsu Moriya, Kohei Shoji, Shinichiro Yoneda, Reiko Ikeda, Takeo Konakahara, Norio Sakai
    • Journal Title

      SYNTHESIS-STUTTGART

      Volume: 45 Issue: 23 Pages: 3233-3238

    • DOI

      10.1055/s-0033-1339903

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Indium(III)-Catalyzed Reductive Bromination and Iodination of Carboxylic Acids to Alkyl Bromides and Iodides: Scope, Mechanism, and One-Pot Transformation to Alkyl Halides and Amine Derivatives2013

    • Author(s)
      Toshimitsu Moriya, Shinichiro Yoneda, Keita Kawana, Reiko Ikeda, Takeo Konakahara, Norio Sakai
    • Journal Title

      JOURNAL OF ORGANIC CHEMISTRY

      Volume: 18 Issue: 21 Pages: 10642-10650

    • DOI

      10.1021/jo401529j

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Copper-Catalyzed Three- Five- or Seven-Component Coupling Reactions: The Selective Synthesis of Cyanomethylamines, N,N-Bis(Cyanomethyl)Amines and N,N'-Bis(Cyanomethyl)- Methylenediamines Based on a Strecker-Type Synthesis,2013

    • Author(s)
      Norio Sakai, Nobuaki Takahashi, Daiki Inoda, Reiko Ikeda, Takeo Konakahara
    • Journal Title

      Molecules

      Volume: 18 Issue: 10 Pages: 12488-12499

    • DOI

      10.3390/molecules181012488

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Cobalt-Catalyzed Oxidative α-Cyanation of Tertiary Aromatic Amines with Trimethylsilyl Cyanide and tert-Butyl Hydroperoxide2013

    • Author(s)
      Norio Sakai, Akihiro Mutsuro, Reiko Ikeda, Takeo Konakahar
    • Journal Title

      SYNLETT

      Volume: 24 Issue: 10 Pages: 1283-1285

    • DOI

      10.1055/s-0033-1338937

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Zinc-catalyzed Reduction of Aldehydes with a Hydrosilane Leading to Symmetric Ethers and Silyl Ethers2013

    • Author(s)
      Norio Sakai, Yoshifumi Nonomura, Reiko Ikeda, Takeo Konakahara
    • Journal Title

      CHEMISTRY LETTERS

      Volume: 42 Issue: 5 Pages: 489-491

    • DOI

      10.1246/cl.121297

    • NAID

      10031167800

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] パラジウム触媒による塩化アシルまたはフッ化アシルと有機ケイ素試薬を用いたベンゾフェノン誘導体の合成2016

    • Author(s)
      﨑野大輔、荻原陽平、坂井教郎
    • 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] コバルト触媒を用いたN-メチルアニリン類とオレフィンの酸化的環化によるキノリン誘導体の合成2016

    • Author(s)
      松本舜、荻原陽平、坂井教郎
    • 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] パラジウム触媒によるアニリンとアレニルエステルの酸化的環化を経るインドール骨格構築法の開発2016

    • Author(s)
      榎本皓太、荻原陽平、坂井教郎
    • 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] One-pot preparation of tetralin derivatives by indium(III)-catalyzed reductive iodination and intramolecular cyclization of 3-benzoylpropionic acids2015

    • Author(s)
      Taichi Kobayashi; Yohei Ogiwara; Norio Sakai
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Knoevenagel condensation of aldehydes and activated methylenes using indium chloride with acetic anhydride as a promoter2015

    • Author(s)
      Keita Takahashi; Takefumi Kitazawa; Yohei Ogiwara; Norio Sakai
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] One-pot preparation of α-aminonitriles by indium-catalyzed three-component coupling reaction of alkynes, amines, and trimethylsilyl cyanide2015

    • Author(s)
      Yuta Hamachi; Yohei Ogiwara; Norio Sakai
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Indium-catalyzed reductive annulation of keto acids with primary amines leading to N-substituted lactams2015

    • Author(s)
      Takuya Uchiyama; Yohei Ogiwara; Norio Sakai
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Copper-catalyzed one-pot synthesis of indoles from anilines and propargylic acetates2015

    • Author(s)
      Kota Enomoto; Mitsumasa Takayanagi; Takeo Konakahara; Yohei Ogiwara; Norio Sakai
    • Organizer
      Pacifichem 2015
    • Place of Presentation
      Honolulu (USA)
    • Year and Date
      2015-12-15
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] インジウム触媒による t-ブチルメルカプタンを硫黄源とした脂肪族カルボン酸と芳香族カルボン酸 からの非対称型チオエーテルの還元的合成2015

    • Author(s)
      良元俊介、宮崎隆弘、荻原陽平、坂井教郎
    • Organizer
      第42回有機典型元素化学討論会
    • Place of Presentation
      名古屋大学 野依記念学術交流館
    • Year and Date
      2015-12-03
    • Related Report
      2015 Annual Research Report
  • [Presentation] 臭化インジウムによる末端アルキンとアルデヒドの酸化的カップリング反応の開発2015

    • Author(s)
      久保田真仁、黒木康太郎、荻原陽平、小中原猛雄、坂井教郎
    • Organizer
      第70回有機合成化学協会関東支部シンポジウム 新潟(長岡)シンポジウム
    • Place of Presentation
      長岡工業高等専門学校
    • Year and Date
      2015-11-21
    • Related Report
      2015 Annual Research Report
  • [Presentation] ヨウ化インジウムを用いたベンジルアルコール類と単体硫黄からの対称型チオエーテルの合成2015

    • Author(s)
      片山正大、宮崎隆弘、荻原陽平、坂井教郎
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] インジウム触媒を用いた第一級ベンジルアルコールのOppenauer酸化反応2015

    • Author(s)
      小野裕司、荻原陽平、坂井教郎
    • Organizer
      第5回CSJ化学フェスタ
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] インジウム触媒による無水酢酸を用いた様々なアルデヒドと活性メチレンとのKnoevenagel反応2015

    • Author(s)
      高橋慶多、北澤毅史、荻原陽平、坂井教郎
    • Organizer
      第32回有機合成化学セミナー
    • Place of Presentation
      ニューウェルシティ湯河原
    • Year and Date
      2015-09-15
    • Related Report
      2015 Annual Research Report
  • [Presentation] インジウム触媒による第1級アミンとケト酸の還元的アミノ化を経るN-置換ラクタム合成2015

    • Author(s)
      内山拓也、荻原陽平、坂井教郎
    • Organizer
      第69回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      横浜国立大学
    • Year and Date
      2015-05-16
    • Related Report
      2015 Annual Research Report
  • [Presentation] インジウム触媒によるエステルとチオールを用いた還元的スルフィド合成2015

    • Author(s)
      笠井辰星、宮崎隆弘、小中原猛雄、荻原陽平、坂井教郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 塩化銅(II)触媒によるプロパルギルアミンとN,O-アセタールの[4+1]分子間環化反応: 多置換ピロール誘導体の新規合成法2015

    • Author(s)
      堀 洋章、荻原陽平、坂井教郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] インジウム触媒を用いたアルキン、アミン、トリメチルシリルシアニドからの三成分連結反応によるα-アミノニトリル合成2015

    • Author(s)
      濱地勇太、荻原陽平、坂井教郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] インジウム触媒を用いたケト酸と第1級アミンの還元的直接アミノ化によるN-置換ラクタムのワンポット合成2015

    • Author(s)
      内山拓也、荻原陽平、坂井教郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] パラジウム触媒を用いたハロゲン化アシルと有機ケイ素試薬とのカップリング反応によるケトン合成法2015

    • Author(s)
      前川祐毅、荻原陽平、坂井教郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] インジウム触媒によるカルボン酸を用いた芳香族化合物の還元的モノアルキル化反応2015

    • Author(s)
      高山健太郎、森谷敏光、小中原猛雄、荻原陽平、坂井教郎
    • Organizer
      日本化学会第95春季年会
    • Place of Presentation
      日本大学理工学部キャンパス
    • Year and Date
      2015-03-26 – 2015-03-29
    • Related Report
      2014 Research-status Report
  • [Presentation] インジウム化合物によるカルボン酸から臭化アルキル及びヨウ化アルキルへの還元的分子変換法とその応用2014

    • Author(s)
      坂井教郎
    • Organizer
      岐阜大学工学部 大学院特別セミナー
    • Place of Presentation
      岐阜大学工学部
    • Year and Date
      2014-12-08
    • Related Report
      2014 Research-status Report
    • Invited
  • [Presentation] インジウム触媒による芳香族カルボニル化合物と単体硫黄からの対称チオエーテル合成2014

    • Author(s)
      良元俊介、宮崎隆弘、西野晃太、荻原陽平、坂井教郎
    • 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
    • Year and Date
      2014-11-27 – 2014-11-29
    • Related Report
      2014 Research-status Report
  • [Presentation] 塩化銅(II)触媒によるプロパルギルアミンとN,O-アセタールを用いたピロール誘導体の新規合成法2014

    • Author(s)
      堀 洋章、荻原陽平、坂井教郎
    • Organizer
      第4回CSJ化学フェスタ2014
    • Place of Presentation
      タワーホール船堀
    • Year and Date
      2014-10-16
    • Related Report
      2014 Research-status Report
  • [Presentation] Copper-Catalyzed Oxidative Nitrosation of Aromatic Secondary Amines Using Nitromethanes2014

    • Author(s)
      佐々木成、荻原陽平、坂井教郎
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学病院キャンパス
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] Indium-Catalyzed Reductive Conversion of Esters to Alkyl Bromides or Alkyl Iodides2014

    • Author(s)
      松下陽平、荻原陽平、小中原猛雄、坂井教郎
    • Organizer
      第61回有機金属化学討論会
    • Place of Presentation
      九州大学病院キャンパス
    • Year and Date
      2014-09-23 – 2014-09-25
    • Related Report
      2014 Research-status Report
  • [Presentation] 銅触媒によるアニリン類とプロパルギルアルコール誘導体を用いたインドール合成反応2014

    • Author(s)
      榎本皓太、高柳光正、小中原猛雄、荻原陽平、坂井教郎
    • Organizer
      第44回複素環化学討論会
    • Place of Presentation
      札幌市民ホール
    • Year and Date
      2014-09-10 – 2014-09-12
    • Related Report
      2014 Research-status Report
  • [Presentation] Indium(III)-Catalyzed Reductive One-Pot Synthesis of Thioethers from Aromatic Aldehydes and Elemental Sulfur2014

    • Author(s)
      Takahiro Miyazaki, Kouta Nishino, Takeo Konakahara, Norio Sakai
    • Organizer
      ISOCS 26
    • Place of Presentation
      トルコ イスタンブール工科大
    • Year and Date
      2014-08-23 – 2014-08-29
    • Related Report
      2014 Research-status Report
  • [Presentation] Gallium(III)-Catalyzed Reductive Chlorination of Carboxylic Acids with Copper(II) Chloride2014

    • Author(s)
      Takumi Nakajima, Shinichiro Yoneda, Yohei Ogiwara, Takeo Konakahara, Norio Sakai
    • Organizer
      ICOMC 26
    • Place of Presentation
      ロイトン札幌
    • Year and Date
      2014-07-13 – 2014-07-19
    • Related Report
      2014 Research-status Report
  • [Presentation] Indium-Catalyzed Reductive Sulfidation of Aromatic Aldehydes with an Elemental Sulfur2014

    • Author(s)
      Takahiro Miyazaki, Kouta Nishino, Takeo Konakahara, Norio Sakai
    • Organizer
      ICOMC 26
    • Place of Presentation
      ロイトン札幌
    • Year and Date
      2014-07-13 – 2014-07-19
    • Related Report
      2014 Research-status Report
  • [Presentation] Copper(I)-Catalyzed Aminomethylation of Boronic Acids with N,O-acetals Leading to α-Arylglycines, Diarylaminomethanes and Benzylamines Derivatives2014

    • Author(s)
      Hiroaki Hori, Yoshihiro Yoshida, Yohei Ogiwara, Takeo Konakahara, Norio Sakai
    • Organizer
      ICOMC 26
    • Place of Presentation
      ロイトン札幌
    • Year and Date
      2014-07-13 – 2014-07-19
    • Related Report
      2014 Research-status Report
  • [Presentation] Friedel-Craftsアシル化と分子内アンニュレーションを組み合わせたテトラリン誘導体の還元的合成2014

    • Author(s)
      小林太一、坂井教郎
    • Organizer
      第3回JACI/GSCシンポジウム
    • Place of Presentation
      東京フォーラム
    • Year and Date
      2014-05-23
    • Related Report
      2014 Research-status Report
  • [Presentation] 銅トリフラートを用いたニトロメタン/DBU系による芳香族二級アミンの酸化的ニトロソ化反応とその応用2014

    • Author(s)
      佐々木成、坂井教郎
    • Organizer
      第3回JACI/GSCシンポジウム
    • Place of Presentation
      東京フォーラム
    • Year and Date
      2014-05-23
    • Related Report
      2014 Research-status Report
  • [Presentation] インジウムトリフラートとトリエチルシランによるニトロベンゼンからアゾベンゼンへの選択的変換2014

    • Author(s)
      浅間駿、坂井教郎
    • Organizer
      第3回JACI/GSCシンポジウム
    • Place of Presentation
      東京フォーラム
    • Year and Date
      2014-05-23
    • Related Report
      2014 Research-status Report
  • [Presentation] 塩化インジウムと酸無水物を用いた芳香族アルデヒドと活性メチレン化合物からのKnoevenagel反応2014

    • Author(s)
      高橋慶多、坂井教郎
    • Organizer
      第67回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      慶應義塾大学矢上キャンパス
    • Year and Date
      2014-05-17
    • Related Report
      2014 Research-status Report
  • [Presentation] インジウム触媒によるカルボン酸から脂肪族ニトリルへの還元的ワンポット合成法

    • Author(s)
      庄子康平・森谷敏光・小中原猛雄・坂井教郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 亜鉛トリフラートを触媒として用いた還元的カップリングによるアルデヒドからエーテルへの一段階変換法

    • Author(s)
      野々村美史・小中原猛雄・坂井教郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] インジウム触媒を用いるカルボン酸とフェノールからのフェニルエステル合成とそのフェニルエーテル誘導体合成への応用

    • Author(s)
      前川祐毅・小中原猛雄・坂井教郎
    • Organizer
      日本化学会第94春季年会
    • Place of Presentation
      名古屋大学
    • Related Report
      2013 Research-status Report
  • [Presentation] インジウム触媒によるカルボン酸とジスルフィドからの還元的カップリング反応を用いた一段階チオエーテル合成

    • Author(s)
      谷ツ田拓磨・宮崎隆弘・森谷敏光・小中原猛雄・坂井教郎
    • Organizer
      第40回有機典型元素化学討論会
    • Place of Presentation
      近畿大学
    • Related Report
      2013 Research-status Report
  • [Presentation] インジウム触媒を用いるエステルとチオールからの還元的チオエーテル合成

    • Author(s)
      笠井辰星・宮崎隆弘・森谷敏光・小中原猛雄・坂井教郎
    • Organizer
      第66回有機合成化学協会関東支部シンポジウム
    • Place of Presentation
      東京工業大学
    • Related Report
      2013 Research-status Report
  • [Presentation] インジウム触媒を用いるエステルの還元的ヨウ素化法

    • Author(s)
      松下陽平・池田玲子・小中原猛雄・坂井教郎
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学医学部
    • Related Report
      2013 Research-status Report
  • [Presentation] 銅(I)- 銅(II) 共触媒を用いたアミン、ホルムアルデヒド、トリメチルシリルシアニドからの多成分連結反応

    • Author(s)
      高橋伸明・猪田大樹・池田玲子・小中原猛雄・坂井教郎
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学医学部
    • Related Report
      2013 Research-status Report
  • [Presentation] 塩化コバルトを用いたトリメチルシリルシアニドによる芳香族第三級アミンの酸化的シアノ化とその応用

    • Author(s)
      無津呂章宏・池田玲子・小中原猛雄・坂井教郎
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学医学部
    • Related Report
      2013 Research-status Report
  • [Presentation] インジウム触媒による芳香族カルボン酸と単体硫黄からの還元的チオエーテル合成

    • Author(s)
      宮崎隆弘・池田玲子・小中原猛雄・坂井教郎
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      九州大学医学部
    • Related Report
      2013 Research-status Report
  • [Presentation] ルイス酸触媒によるインドールあるいはピロールへのアミノメチル化の位置選択的制御

    • Author(s)
      坂井教郎・岡野秀俊・池田玲子・小中原猛雄
    • Organizer
      第43回複素環化学討論会
    • Place of Presentation
      岐阜市長良川国際会議場
    • Related Report
      2013 Research-status Report
  • [Presentation] Direct Chlorination of Carboxylic Acids by GaCl3-Catalyzed Reduction

    • Author(s)
      Takumi Nakajima, Toshimitsu Moriya, Shinichiro Yoneda, Reiko Ikeda, Takeo Konakahara, Norio Sakai
    • Organizer
      第60回有機金属化学討論会
    • Place of Presentation
      学習院大学
    • Related Report
      2013 Research-status Report
  • [Presentation] 臭化銅を用いるボロン酸とN,O-アセタールからのα-アリールグリシン誘導体の新規合成法

    • Author(s)
      堀 洋章、浅野順一、池田玲子、小中原猛雄、坂井教郎
    • Organizer
      第65回有機合成化学協会関東支部(新潟)シンポジウム
    • Place of Presentation
      新潟薬科大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ヨウ化インジウムを用いたカルボン酸による芳香族化合物の還元的モノアルキル化反応

    • Author(s)
      高山健太郎、森谷敏光、池田玲子、小中原猛雄、坂井教郎
    • Organizer
      第65回有機合成化学協会関東支部(新潟)シンポジウム
    • Place of Presentation
      新潟薬科大学
    • Related Report
      2013 Research-status Report
  • [Presentation] ヨウ化インジウムによるヒドロシラン類を用いたニトロベンゼンからアニリンへの化学選択的変換法の開発

    • Author(s)
      浅間 駿、森谷敏光、池田玲子、小中原猛雄、坂井教郎
    • Organizer
      第65回有機合成化学協会関東支部(新潟)シンポジウム
    • Place of Presentation
      新潟薬科大学
    • Related Report
      2013 Research-status Report
  • [Remarks] 東京理科大学坂井研究室HP

    • URL

      http://www.rs.tus.ac.jp/sakaigroup/site/Home.html

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
  • [Remarks] 東京理科大学坂井研究室HP

    • URL

      http://www.rs.tus.ac.jp/sakaigroup/site/Home.html

    • Related Report
      2013 Research-status Report

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Published: 2014-07-25   Modified: 2019-07-29  

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