• Search Research Projects
  • Search Researchers
  • How to Use
  1. Back to project page

2011 Fiscal Year Final Research Report

Development of nucleophilic cyanation to non-activated alkynes

Research Project

  • PDF
Project/Area Number 21590003
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionChiba University

Principal Investigator

ARAI Shigeru  千葉大学, 大学院・薬学研究院, 准教授 (20285224)

Project Period (FY) 2009 – 2011
Keywordsアルキン / シアノ化 / パラジウム / 触媒
Research Abstract

Nucleophilic cyanation has been developed by using catalytic amount of Pd(II) with non-activated alkynes and CN source. This fundamental and non-reported transformation in organometallic chemistry is named as cyanopalladation which promote electrophilic activation of alkynes and smooth nucleophilic attack from external CN source such as TMSCN. Furthermore, enynes and dienynes which have conjugated enyne units have been found for quite suitable substrates to install CN functionality in regio- and stereoselective fashion through cyclization protocol.

  • Research Products

    (16 results)

All 2011 2010 2009

All Journal Article (6 results) (of which Peer Reviewed: 6 results) Presentation (9 results) Book (1 results)

  • [Journal Article] Catalytic Dicyanative [4+2]Cycloaddition Triggered byCyanopalladation Using Ene-enynesand Cyclic Enynes with MethylAcrylate2010

    • Author(s)
      Arai, S, , Koike, Y., Hada, H., Nishida, A
    • Journal Title

      J. Org. Chem

      Volume: 75 Pages: 7573-7579

    • Peer Reviewed
  • [Journal Article] Catalytic Dicyanative [4+2]Cycloaddition Triggered byCyanopalladation of ConjugatedEnynes Under Aerobic Conditions2010

    • Author(s)
      Arai, S, , Koike, Y., Hada, H, Nishida, A.
    • Journal Title

      J. Am. Chem. Soc

      Volume: 132 Pages: 4522-4523,11824 (addition/correction).

    • Peer Reviewed
  • [Journal Article] Catalytic Dicyanative 5-exo- and6-endo-Cyclization Triggered by Cyanopalladation of Alkynes2010

    • Author(s)
      Arai, S, , Koike, Y., Nishida, A
    • Journal Title

      Adv. Synth. Catal

      Volume: 352 Pages: 893-900

    • Peer Reviewed
  • [Journal Article] Palladium-Catalyzed Cyanation of Carbon-Carbon Triple Bonds under Aerobic Conditions2010

    • Author(s)
      Arai S., Sato T., Koike Y., Hayashi M., Nishida A
    • Journal Title

      Angew. Chem. Int. Ed, Highlighted in Synth. Org. Chem. Jpn

      Volume: 48,68 Pages: 4528-4531,567

    • Peer Reviewed
  • [Journal Article] Asymmetric Synthesis of Hydroisoquinoline Derivatives, a Key Intermediate for Manzamine Synthesis, by Diels-Alder Reaction Using 4-Amino-2-siloxybutadiene2009

    • Author(s)
      Mihara Y., Matsumura T., Terauchi Y., Akiba M., Arai S., Nishida, A
    • Journal Title

      Bull. Chem. Soc. Jpn

      Volume: 82 Pages: 1520-1527

    • Peer Reviewed
  • [Journal Article] Catalytic 1,2-Dicyanation of Alkynes by Palladium(II) under Aerobic Conditions2009

    • Author(s)
      Arai S, Sato T., Nishida A
    • Journal Title

      Adv. Synth. Catal

      Volume: 351,11 Pages: 1897-1904,1225

    • Peer Reviewed
  • [Presentation] パラジウム触媒を用いるアルキンのシアノ化2011

    • Author(s)
      荒井秀, 小池由佳, 五十嵐知宏, 楊暁菲, 西田篤司
    • Organizer
      第37回反応と合成の進歩シンポジウム講演要旨集
    • Place of Presentation
      徳島
    • Year and Date
      2011-11-07
  • [Presentation] シクロプロパン融合型院疎林骨格を有するLundurine類の合成研究2011

    • Author(s)
      星真幸, 金子統, 荒井秀, 西田篤司
    • Organizer
      第41回複素環化学討論会講演要旨集
    • Place of Presentation
      崇城大学市民ホール
    • Year and Date
      2011-10-22
  • [Presentation] 炭素-炭素多重結合への触媒的シアノ化を基軸とする環化反応2011

    • Author(s)
      天児由佳, 荒井秀, 西田篤司
    • Organizer
      第55回日本薬学会関東支部大会講演要旨集
    • Place of Presentation
      東邦大学
    • Year and Date
      2011-10-08
  • [Presentation] Pd-Catalyzed Cyanation of Non-activated Alkynes2011

    • Author(s)
      Shigeru Arai, Yuka Koike, Tomohiro Igarashi, Xiaofei Yang, Atsushi Nishida
    • Organizer
      58th Symposium on Organometallic Chemistry, Japan
    • Place of Presentation
      Nagoya
    • Year and Date
      2011-09-08
  • [Presentation] アルキンの触媒的シアノ化と環化反応への応用2010

    • Author(s)
      小池由佳, 羽田博彦, 荒井秀, 西田篤司
    • Organizer
      日本薬学会第130年会講演プログラム
    • Place of Presentation
      岡山
    • Year and Date
      2010-03-30
  • [Presentation] Palladium catalyzed cyanation of alkynes and its application2010

    • Author(s)
      Shigeru Arai, Yuka Koike, Atsushi Nishida
    • Organizer
      American Chemical Society 239^<th>National Meeting
    • Place of Presentation
      San Francisco, CA
    • Year and Date
      2010-03-23
  • [Presentation] パラジウム触媒.酸素系におけるシアノ基導入型環化反応2009

    • Author(s)
      小池由佳, 羽田博彦, 荒井秀, 西田篤司
    • Organizer
      第39回複素環化学討論会講演要旨集
    • Place of Presentation
      柏
    • Year and Date
      2009-10-15
  • [Presentation] パラジウム触媒.酸素系におけるエンイン化合物のシアノ基導入型環化反応2009

    • Author(s)
      小池由佳, 佐藤崇, 林迪乃, 荒井秀, 西田篤司
    • Organizer
      第25回有機合成化学セミナー講演要旨集
    • Place of Presentation
      阿蘇
    • Year and Date
      2009-09-09
  • [Presentation] パラジウム触媒によるアルキンのシアノ化と環化反応への応用2009

    • Author(s)
      荒井秀, 小池由佳, 西田篤司
    • Organizer
      第3回日本化学会関東支部大会講演要旨集
    • Place of Presentation
      早稲田
    • Year and Date
      2009-09-04
  • [Book] 触媒的二重シアノ環化反応,ワンポットジアゾアルドール反応,使える!有機合成反応241実践ガイド2010

    • Author(s)
      西田篤司, 荒井秀, 西田篤司, 荒井秀, 丸岡啓二, 他
    • Total Pages
      146-147,250-251

URL: 

Published: 2013-07-31  

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi