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Efficient Nucleophilic Addition to Haloacetylenes and Its Application

Research Project

Project/Area Number 22655014
Research Category

Grant-in-Aid for Challenging Exploratory Research

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionTokyo Institute of Technology

Principal Investigator

URABE Hirokazu  東京工業大学, 大学院・生命理工学研究科, 教授 (10176745)

Project Period (FY) 2010 – 2011
Project Status Completed (Fiscal Year 2011)
Budget Amount *help
¥3,420,000 (Direct Cost: ¥3,000,000、Indirect Cost: ¥420,000)
Fiscal Year 2011: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000)
Fiscal Year 2010: ¥1,600,000 (Direct Cost: ¥1,600,000)
Keywordsインドール / 求核付加反応 / スルホンアミド / テトラヒドロフラン / パラジウム / ハロアルキン / ピロール / ヘテロ環化合物 / イミダゾール / カルベン / 触媒反応 / スルホニルエナミン / ロジウム
Research Abstract

When imidazolines, imidazoles, N-allyl-, N-aryl-, or N-propyl-sulfonamides were heated with 1-halo-1-alkynes in DMF, cis-2-hetero groupsubstituted-1-halo-1-alkenes were produced with high regioand stereoselectivities. On treatmen with Pd catalysts, the sulfonamide adducts were led to pyrroles, indoles, and benzothiazine 1, 1-dioxides. Similarly, when amines or alcohols were heated with 1-halo-1-alkynes in DMF, their nucleophilic addition to 1-halo-1-alkynes resulted in the generation of vinyl carbene intermediates, which were intercepted with sodium sulfinate to give 2-hetero group-substituted-1-sulfonyl-1-alkenes.

Report

(3 results)
  • 2011 Annual Research Report   Final Research Report ( PDF )
  • 2010 Annual Research Report
  • Research Products

    (23 results)

All 2012 2011 2010 Other

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (15 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Facile Preparation of Indoles and 1, 2-Benzothiazine 1, 1-Dioxides via Nucleophilic Addition of Sulfonamides to Bromoacetylenes Followed by Pd-Catalyzed Cyclization2012

    • Author(s)
      Masahito Yamagishi, Ken Nishigai, Azusa Ishii, Takeshi Hata, and Hirokazu Urabe
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: (in press) Issue: 26 Pages: 6471-6474

    • DOI

      10.1002/anie.201201024

    • Year and Date
      2012-05-13
    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Additive-free Nucleophilic Addition of Imidazolines and Imidazoles to Haloacetylenes2012

    • Author(s)
      Masahito Yamagishi, Jun Okazaki, Ken Nishigai, Takeshi Hata, and Hirokazu Urabe
    • Journal Title

      Org. Lett.

      Volume: 14 Pages: 34-37

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Additive-free Nucleophilic Addition of Imidazolines and Imidazoles to Haloacetylenes2012

    • Author(s)
      Masahito Yamagishi, Jun Okazaki, Ken Nishigai, Takeshi Hata, Hirokazu Urabe
    • Journal Title

      Org.Lett.

      Volume: 14 Issue: 1 Pages: 34-37

    • DOI

      10.1021/ol2027448

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Facile Preparation of Indoles and 1,2-Benzothiazine 1,1-Dioxides via Nucleophilic Addition of Sulfonamides to Bromoacetylenes Followed by Pd-Catalyzed Cyclization2012

    • Author(s)
      Masahito Yamagishi, Ken Nishigai, Azusa Ishii, Takeshi Hata, Hirokazu Urabe
    • Journal Title

      Angew.Chem.Int.Ed.

      Volume: (in press)

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Nucleophilic Addition of Sulfonamides to Bromoacety lenes : Facile Preparation of Pyrroles2011

    • Author(s)
      Masahito Yamagishi, Ken Nishigai, Takeshi Hata, and Hirokazu Urabe
    • Journal Title

      Org. Lett.

      Volume: 13 Pages: 4873-4875

    • Related Report
      2011 Final Research Report
    • Peer Reviewed
  • [Journal Article] Nucleophilic Addition of Sulfonamides to Bromoacetylenes : Facile Preparation of Pyrroles2011

    • Author(s)
      Masahito Yamagishi, Ken Nishigai, Takeshi Hata, Hirokazu Urabe
    • Journal Title

      Org.Lett.

      Volume: 13 Issue: 18 Pages: 4873-4875

    • DOI

      10.1021/ol201952b

    • Related Report
      2011 Annual Research Report
    • Peer Reviewed
  • [Presentation] ハロアセチレンへの求核付加とC-H活性化環化による簡便なインドールの合成2012

    • Author(s)
      山岸優仁・石井梓・秦猛志・占部弘和
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学日吉キャンパス
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] ハロアセチレンへの求核付加とC-H活性化環化による簡便な1, 2-ベンゾチアジン1, 1-ジオキシドの合成2012

    • Author(s)
      西海憲・山岸優仁・秦猛志・占部弘和
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学日吉キャンパス
    • Year and Date
      2012-03-26
    • Related Report
      2011 Final Research Report
  • [Presentation] ハロアセチレンへの求核付加とC-H活性化環化による簡便なジヒドロイソキノリンの合成2012

    • Author(s)
      山岸優仁・石井梓・秦猛志・占部弘和
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学日吉キャンパス
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report 2011 Final Research Report
  • [Presentation] ハロアセチレンへの求核付加とC-H活性化環化による簡便な1,2-ベンゾチアジン1,1-ジオキシドの合成2012

    • Author(s)
      西海憲・山岸優仁・秦猛志・占部弘和
    • Organizer
      日本化学会第92春季年会
    • Place of Presentation
      慶応大学日吉キャンパス
    • Year and Date
      2012-03-26
    • Related Report
      2011 Annual Research Report
  • [Presentation] 1-ハロ-1-アルキンへの求核付加反応とその利用2011

    • Author(s)
      山岸優仁・西海憲・岡崎純・秦猛志・占部弘和
    • Organizer
      第99回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学薬学部マルチメディア講堂
    • Year and Date
      2011-06-16
    • Related Report
      2011 Final Research Report
  • [Presentation] 1-ハロ-1-アルキンへの求核付加反応とその利用2011

    • Author(s)
      山岸優仁・西海憲・岡崎純・秦猛志・占部弘和
    • Organizer
      第99回有機合成シンポジウム
    • Place of Presentation
      慶應義塾大学薬学部(東京都)
    • Year and Date
      2011-06-16
    • Related Report
      2011 Annual Research Report
  • [Presentation] 5-ハロ-4-アルキン-1-オールの求核的環化反応及び求核的環化スルホニル化反応2011

    • Author(s)
      山岸優仁・岡崎純・秦猛志・占部弘和
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2011 Final Research Report
  • [Presentation] ハロアセチレンへの求核付加反応を基軸とする環状アミンの合成2011

    • Author(s)
      山岸優仁・岡崎純・秦猛志・占部弘和
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2011 Final Research Report
  • [Presentation] ハロアセチレンへのイミダゾール・イミダゾリンの立体選択的求核付加反応2011

    • Author(s)
      山岸優仁・西海憲・岡崎純・秦猛志・占部弘和
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh触媒によるハロアセチレンと芳香環の分子内環化反応とその利用2011

    • Author(s)
      妹尾麻慧・千田浩介・秦猛志・占部弘和
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学横浜キャンパス
    • Year and Date
      2011-03-26
    • Related Report
      2011 Final Research Report
  • [Presentation] Rh触媒によるハロアセチレンと芳香環の分子内環化反応とその利用2011

    • Author(s)
      妹尾・千田・秦・占部
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜)
    • Year and Date
      2011-03-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] ハロアセチレンへのイミダゾール・イミダゾリンの立体選択的求核付加反応2011

    • Author(s)
      西海・山岸・岡崎・秦・占部
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜)
    • Year and Date
      2011-03-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] ハロアセチレンへの求核付加反応を基軸とする環状アミンの合成2011

    • Author(s)
      山岸・岡崎・秦・占部
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜)
    • Year and Date
      2011-03-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] 5-ハロ-4-アルキン-1-オールの求核的環化反応及び求核的環化スルホニル化反応2011

    • Author(s)
      山岸・岡崎・秦・占部
    • Organizer
      日本化学会第91春季年会
    • Place of Presentation
      神奈川大学(横浜)
    • Year and Date
      2011-03-26
    • Related Report
      2010 Annual Research Report
  • [Presentation] ロジウム触媒によるハロアセチレンと含窒素官能基置換芳香環の分子内環化反応(Rh-Catalyzed Intramolecular Cyclization of Haloacetylene and Nitrogen Group-Substituted Aromatic Ring)2010

    • Author(s)
      妹尾麻慧・千田浩介・村瀬裕彦・秦猛志・占部弘和
    • Organizer
      第57回有機金属化学討論会
    • Place of Presentation
      中央大学
    • Year and Date
      2010-09-16
    • Related Report
      2011 Final Research Report
  • [Book] 第4章芳香族化合物-医薬品化学への展開、生命理工系のための大学院基礎講座-有機化学、湯浅英哉・編2011

    • Author(s)
      占部弘和、秦猛志
    • Publisher
      東京工業大学出版会・工学図書
    • Related Report
      2011 Final Research Report
  • [Remarks]

    • URL

      http://www.urabe-lab.bio.titech.ac.jp

    • Related Report
      2011 Final Research Report

URL: 

Published: 2010-08-23   Modified: 2016-04-21  

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