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Development of multi-tunable templates for synthesis of differentially all-carbon tetrasubstituted olefins

Research Project

Project/Area Number 15K05507
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeMulti-year Fund
Section一般
Research Field Synthetic chemistry
Research InstitutionRyukoku University

Principal Investigator

Iwasawa Tetsuo  龍谷大学, 理工学部, 教授 (80452655)

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選択的合成 / 四置換アルケン合成 / ビニルハロゲン / ビニルシラン / ハロゲン脱離 / 異種炭素四置換アルケン / 選択的シアノ化 / 四置換アルケン / ハロゲン化 / シアノ化 / 臭素選択的反応 / ヨウ素選択的反応
Outline of Final Research Achievements

Development of a simple, rationale, and stereo-defined synthesis of differentially all-carbon tetrasubstituted olefins were performed: vicinal (Z)-dihaloalkenyl silanes were successfully synthesized via addition of in situ generated XX’ to silylethynylarenes, and the vinyl dihalides were employed as synthetic scaffolds for preparation of tetrasubstituted alkenes. When the scaffolds were attempted in the halogen-selective substitution reactions, they suffered from the beta-halogen elimination to put them back to original alkynes; finally, the scaffolds successfully undertook the chemo-selective carbon-carbon bond-forming reactions. This new finding will lead us to synthesis of tetrasubstituted olefins although we don’t yet solve the problematic halogen-elimination side-reactions and simple routes to the olefins.

Report

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

    (12 results)

All 2018 2017 2016 Other

All Journal Article (3 results) (of which Peer Reviewed: 3 results,  Acknowledgement Compliant: 2 results) Presentation (7 results) (of which Int'l Joint Research: 1 results) Remarks (2 results)

  • [Journal Article] Regio-selective cyanation of (Z)-(1,2-dibromo-2-arylvinyl)triisopropylsilane with suppression of halogen elimination2017

    • Author(s)
      Naoki Endo, Kazunari Goto, Koshi Murakami, Tetsuo Iwasawa
    • Journal Title

      Tetrahedron Letters

      Volume: 58 Issue: 19 Pages: 18421845-18421845

    • DOI

      10.1016/j.tetlet.2017.03.082

    • Related Report
      2017 Annual Research Report 2016 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Journal Article] Stereo-defined synthesis of differentially all-carbon Tetrasubstituted olefins derived from (E)-1-bromo-2-iodoalkenes2017

    • Author(s)
      N. Endo, T. Iwasawa
    • Journal Title

      Tetrahedron

      Volume: 73 Issue: 40 Pages: 58335840-58335840

    • DOI

      10.1016/j.tet.2017.08.013

    • Related Report
      2017 Annual Research Report
    • Peer Reviewed
  • [Journal Article] Elucidation of reaction process through beta-halogen elimination in CuCN-mediated cyanation of (E)-1-bromo-2-iodoalkene2016

    • Author(s)
      Naoki Endo, Mao Kanaura, Tetsuo Iwasawa
    • Journal Title

      Tetrahedron Letters

      Volume: 57 Issue: 4 Pages: 483-486

    • DOI

      10.1016/j.tetlet.2015.12.063

    • Related Report
      2016 Research-status Report 2015 Research-status Report
    • Peer Reviewed / Acknowledgement Compliant
  • [Presentation] 四置換アルケン合成を指向したビシナルジハロアルケンの選択的シアノ化2018

    • Author(s)
      遠藤直輝、岩澤哲郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] ビシナルジハロアルケンを足場とする異種炭素四置換アルケンのテンプレート合成開発2018

    • Author(s)
      遠藤直輝、岩澤哲郎
    • Organizer
      日本化学会第98春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] (E)-1-ヨード-2-ブロモアルケンのヨウ素選択的シアノ化反応による四置換alkene合成とその反応過程の考察2017

    • Author(s)
      遠藤直輝、金浦茉央、岩澤哲郎
    • Organizer
      日本化学会第97春季年会
    • Place of Presentation
      神奈川県横浜市 慶應義塾大学日吉キャンパス
    • Year and Date
      2017-03-16
    • Related Report
      2016 Research-status Report
  • [Presentation] (E)-1-ヨード2-ブロモアルケンのヨウ素選択的シアノ化反応による四置換アルケン合成とその反応過程の考察2017

    • Author(s)
      遠藤直輝、金浦茉央、岩澤哲郎
    • Organizer
      日本化学会第97春季年会
    • Related Report
      2017 Annual Research Report
  • [Presentation] 四置換オレフィン合成を指向したビシナルジブロモアルケンの選択的臭素活性化2017

    • Author(s)
      遠藤直輝、岩澤哲郎
    • Organizer
      日本プロセス化学会2017サマーシンポジウム
    • Related Report
      2017 Annual Research Report
  • [Presentation] Elucidation of reaction process through halogen elimination in CuCN-mediated cyanation of (E)-1-bromo-2-iodoalkene2017

    • Author(s)
      遠藤直輝、岩澤哲郎
    • Organizer
      Tetrahedron Symposium
    • Related Report
      2017 Annual Research Report
    • Int'l Joint Research
  • [Presentation] 異種炭素四置換オレフィン型アクリロニトリルの合成とその反応機構2016

    • Author(s)
      遠藤直輝、金浦茉央、岩澤哲郎
    • Organizer
      日本プロセス化学会2016サマーシンポジウム
    • Place of Presentation
      愛知県名古屋市 名古屋国際会議場
    • Year and Date
      2016-07-28
    • Related Report
      2016 Research-status Report
  • [Remarks] 龍谷大学 理工学部 岩澤研究室 publicatin欄

    • URL

      http://www.chem.ryukoku.ac.jp/iwasawa/index.html

    • Related Report
      2017 Annual Research Report
  • [Remarks] 龍谷大学理工学部物質化学科 岩澤研究室

    • URL

      http://www.chem.ryukoku.ac.jp/iwasawa/index.html

    • Related Report
      2015 Research-status Report

URL: 

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

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