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

Development of Unprecedented Catalytic Carbocyanation

Research Project

Project/Area Number 25460004
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Chemical pharmacy
Research InstitutionChiba University

Principal Investigator

Arai Shigeru  千葉大学, 薬学研究科(研究院), 准教授 (20285224)

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: ¥780,000 (Direct Cost: ¥600,000、Indirect Cost: ¥180,000)
Fiscal Year 2014: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Fiscal Year 2013: ¥2,210,000 (Direct Cost: ¥1,700,000、Indirect Cost: ¥510,000)
Keywordsニッケル / 遷移金属触媒 / シアノ化 / 環化 / アルキン / ヒドロシアノ化 / ヒドロシアアノ化 / ニッケル触媒 / アレン / ヒドロアシル化 / コバルト触媒 / アルカロイド合成 / シクロプロパン / 環化反応 / ヘテロ環
Outline of Final Research Achievements

We have developed the discrimination of CC multiple bonds through Ni-catalyzed hydrocyanation and established regio- and stereoselective cyanation of alkynes, allenes, and enynes. These substrates are easily transformed to the corresponding carbonitriles and allene system is particularly effective to obtain a single product through this methodology. Allenyl cyclopropane are also effectively converted to the secondary carbonitriles as a sole product via CC sigma bond cleavage of cyclopropane and further application for the synthesis \of natural products are currently undergoing.

Report

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

    (29 results)

All 2016 2015 2014 2013 Other

All Journal Article (12 results) (of which Peer Reviewed: 12 results,  Acknowledgement Compliant: 4 results,  Open Access: 1 results) Presentation (16 results) (of which Int'l Joint Research: 3 results,  Invited: 1 results) Remarks (1 results)

  • [Journal Article] Furan-Iminium Cation Cyclization (FIC) in A Total Synthesis of Manzamine Alkaloids and A Formal Total Synthesis of Manzamine A. J. Antibiotics, 2016, xx, xxx-xxx. DOI: 102016

    • Author(s)
      A. Nishida, A.; Tokumaru, K.; Ohfusa, T.; Arai, S.
    • Journal Title

      J. Antibiotics

      Volume: 69 Issue: 4 Pages: 340-343

    • DOI

      10.1038/ja.2016.24

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Total Syntheses of (+)-Grandilodine C and (+)-Lapidilectine B; Determination of their Absolute Stereochemistry2016

    • Author(s)
      Nakajima, M.; Arai, S.; Nishida, A.
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 55 Issue: 10 Pages: 3473-3476

    • DOI

      10.1002/anie.201510561

    • Related Report
      2015 Annual Research Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A New Protocol for Nickel-catalysed Regio- and Stereoselective Hydrocyanation of Allenes2015

    • Author(s)
      Arai, S.; Hori, H.; Amako, Y.; Nishida, A.
    • Journal Title

      Chem. Commun.

      Volume: 51 Issue: 35 Pages: 7493-7496

    • DOI

      10.1039/c5cc01899d

    • Related Report
      2015 Annual Research Report 2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Asymmetric Total Synthesis of (-)-Lundurine B and Determination of Its Absolute Stereochemistry2015

    • Author(s)
      Nakajima, M.; Arai, S.; Nishida, A.
    • Journal Title

      Chem. Asian J.

      Volume: 10 Issue: 4 Pages: 1065-1070

    • DOI

      10.1002/asia.201403407

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] A Concise and Versatile Synthesis of Alkaloids from Kopsia tenuis: Total Synthesis of (±)-Lundurine A and B2014

    • Author(s)
      Shigeru Arai, Masaya Nakajima, Atsushi Nishida
    • Journal Title

      Angew. Chem. Int. Ed.

      Volume: 53 Issue: 22 Pages: 5569-5572

    • DOI

      10.1002/anie.201400464

    • Related Report
      2014 Research-status Report
    • Peer Reviewed / Open Access / Acknowledgement Compliant
  • [Journal Article] Total synthesis of (±)-lundurine B2014

    • Author(s)
      Hoshi, M., Kaneko, O., Nakajima, M., Arai, S., Nishida, A.
    • Journal Title

      Organic Letters

      Volume: 16 Issue: 3 Pages: 768-771

    • DOI

      10.1021/ol4034786

    • Related Report
      2014 Research-status Report 2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] A 2-Benzothiazolylphenyl Group Accelerates the Intramolecular [2+2] Cycloaddition of Allene-ynes2014

    • Author(s)
      Hori, H.; Arai, S.; Nishida, A.
    • Journal Title

      Asian Journal of Organic Chemistry

      Volume: 3 Issue: 1 Pages: 41-43

    • DOI

      10.1002/ajoc.201300218

    • Related Report
      2014 Research-status Report 2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Anti-carbocyanative Cyclization of Enynes under Nickel Catalysis2013

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

      Journal of Organic Chemistry

      Volume: 78 Issue: 9 Pages: 4366-4372

    • DOI

      10.1021/jo400342y

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Hydrocyanative Cyclization and Three-component Cross-coupling Reaction between Allenes and Alkynes under Nickel Catalysis2013

    • Author(s)
      Arai, S.; Amako, Y.; Yang, X.; Nishida, A
    • Journal Title

      Angewandte Chemie International Edition

      Volume: 52 Issue: 31 Pages: 8147-8150

    • DOI

      10.1002/anie.201303883

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Catalytic Cyanation of Carbon-Carbon Triple Bonds Through a Three-Component Cross-coupling Reaction under Nickel Catalysis2013

    • Author(s)
      Yang, X.; Arai, S.; Nishida, A.
    • Journal Title

      Advanced Synthesis & Catalysis

      Volume: 355 Issue: 14-15 Pages: 2974-2981

    • DOI

      10.1002/adsc.201300553

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Regioselective Hydronickelation of Allenes and Its Application to the Hydrocyanative Carbocyclization Reaction of Allene-ynes and Bis-allenes2013

    • Author(s)
      Amako, Y.; Hori H.; Arai, S.; Nishida, A.
    • Journal Title

      Journal of Organic Chemistry

      Volume: 78 Issue: 21 Pages: 10763-10775

    • DOI

      10.1021/jo401758v

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Journal Article] Total synthesis of schizocommunin and revision of its structure2013

    • Author(s)
      Uehata, K., Kimura, N., Hasegawa, K., Arai, S., Nishida, M., Hosoe, T., Kawai, K.-I., Nishida, A.
    • Journal Title

      Journal of Natural Products

      Volume: 76 Issue: 11 Pages: 2034-2039

    • DOI

      10.1021/np400263f

    • Related Report
      2013 Research-status Report
    • Peer Reviewed
  • [Presentation] 6.アルケンとアシルホスホナートを用いるコバルト触媒環化反応2016

    • Author(s)
      堀弘人
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] アレンの位置および立体選択的ヒドロシアノ化とアルカロイド合成への応用2016

    • Author(s)
      松本光希
    • Organizer
      日本薬学会第136年会
    • Place of Presentation
      横浜
    • Year and Date
      2016-03-27
    • Related Report
      2015 Annual Research Report
  • [Presentation] Asymmetric Total Synthesis of Kopsia Alkaloids2016

    • Author(s)
      Shigeru Arai
    • Organizer
      251st ACS National Meeting and Exposition
    • Place of Presentation
      サンディエゴ
    • Year and Date
      2016-03-13
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Grandilodine C及び関連アルカロイドの全合成研究2015

    • Author(s)
      中島誠也
    • Organizer
      第108回有機合成シンポジウム
    • Place of Presentation
      早稲田大学
    • Year and Date
      2015-11-05
    • Related Report
      2015 Annual Research Report
  • [Presentation] Regio- and Stereoselective Hydrocycnation of Allenes through Cyclopropane Cleavage under Nickel Catalysis2015

    • Author(s)
      Hiroto Hori
    • Organizer
      The 5tn Junior International Conference on Cutting-Edge Organic Chemistry
    • Place of Presentation
      Taiwan
    • Year and Date
      2015-11-02
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] ニッケル触媒によるアレンの位置及び立体選択的ヒドロシアノ化反応2015

    • Author(s)
      天児由佳
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      船堀
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] ランドリン及び関連アルカロイドの全合成2015

    • Author(s)
      中島誠也
    • Organizer
      第5回CSJ化学フェスタ2015
    • Place of Presentation
      船堀
    • Year and Date
      2015-10-13
    • Related Report
      2015 Annual Research Report
  • [Presentation] Ni-Catalyzed Cyanation of CC Multiple Bonds2015

    • Author(s)
      Shigeru Arai
    • Organizer
      講演会
    • Place of Presentation
      Strasbourg University, France
    • Year and Date
      2015-07-04
    • Related Report
      2015 Annual Research Report
    • Invited
  • [Presentation] Nickel-catalyzed cyanation of carbon-carbon multiple bonds2015

    • Author(s)
      Shigeru Arai
    • Organizer
      Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS-18)
    • Place of Presentation
      Sitges, Spain
    • Year and Date
      2015-06-28
    • Related Report
      2015 Annual Research Report
    • Int'l Joint Research
  • [Presentation] Pinpoint Cyanation of CC Multiple Bonds under Nickel Catalysis2014

    • Author(s)
      Shigeru Arai
    • Organizer
      24th International Conference on Organometallic Chemistry
    • Place of Presentation
      Sapporo
    • Year and Date
      2014-07-13 – 2014-07-16
    • Related Report
      2014 Research-status Report
  • [Presentation] PINPOINT CYANAION of sp AND sp2 CARBONS UNDER NICKEL CATALYSIS2014

    • Author(s)
      Shigeru Arai
    • Organizer
      20th International Conference on Organic Synthesis (ICOS-20, L-39)
    • Place of Presentation
      Budapest, Hungary
    • Year and Date
      2014-06-29 – 2014-07-04
    • Related Report
      2014 Research-status Report
  • [Presentation] Nickel-Catalyzed Cyanation of Carbon-carbon Triple Bonds2014

    • Author(s)
      Shigeru Arai
    • Organizer
      247th ACS National Meeting and Exposition
    • Place of Presentation
      Dallas, TX (USA)
    • Related Report
      2013 Research-status Report
  • [Presentation] ニッケル触媒を用いるアルキンのシアノ化反応2013

    • Author(s)
      荒井秀
    • Organizer
      第39回反応と合成の進歩シンポジウム
    • Place of Presentation
      福岡
    • Related Report
      2013 Research-status Report
  • [Presentation] ニッケル触媒によるアレンのヒドロニッケル化を基軸としたシアノ環化反応2013

    • Author(s)
      天児由佳
    • 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] ニッケル触媒を用いるシアノ基導入型3成分カップリング反応の開発2013

    • Author(s)
      楊暁菲
    • 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] ニッケル触媒を用いるシアノ基導入型3成分カップリング反応の開発2013

    • Author(s)
      楊暁菲
    • Organizer
      第57回日本薬学会関東支部大会
    • Place of Presentation
      帝京大学薬学部
    • Related Report
      2013 Research-status Report
  • [Remarks] 千葉大学薬学部薬品合成化学

    • URL

      http://www.p.chiba-u.ac.jp/lab/gousei/index.html

    • Related Report
      2013 Research-status Report

URL: 

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

Information User Guide FAQ News Terms of Use Attribution of KAKENHI

Powered by NII kakenhi