Development of Efficient Synthetic Method of Oligoenes via Selective Linear Oligomerization of Alkynes

• Project/Area Number: 20750160
• Research Category: Grant-in-Aid for Young Scientists (B)
• Allocation Type: Single-year Grants
• Research Field: Organic industrial materials
• Research Institution: Hokkaido University
• Principal Investigator: KANNO Ken-Ichiro Hokkaido University, 触媒化学研究センター, 助教 (20360951)
• Project Period (FY): 2008 – 2009
• Project Status: Completed (Fiscal Year 2009)
• Budget Amount: ¥4,420,000 (Direct Cost: ¥3,400,000、Indirect Cost: ¥1,020,000); Fiscal Year 2009: ¥2,080,000 (Direct Cost: ¥1,600,000、Indirect Cost: ¥480,000); Fiscal Year 2008: ¥2,340,000 (Direct Cost: ¥1,800,000、Indirect Cost: ¥540,000)
• Keywords: 機能性有機材料 / ジルコナシクロペンタジエン / オリゴエン / カルボリチオ化 / 7員環化合物 / アルキン / ジルコニウム / 直鎖状多量化

Research Abstract

Highly selective synthesis of tri-and tetraene derivatives as single products was achieved via linear oligomerization of different alkynes via a zirconocene and copper-mediated reaction. And, interesting 7-membered-ring formation of a triene derivatives obtained from the above-mentioned reaction was found. These reactions were applicable for variously substituted substrates.

Research Products

• [Journal Article] Selective Protonation/Iodination of Unsymmetrical Zirconacyclopentadienes (2010)
  • Author(s): E.Igarashi, S.Ren, K.Kanno, T.Takahashi
  • Journal Title: Chemistry Letters 39 Pages: 350-351
  • NAID: 10027179137
  • Peer Reviewed
• [Presentation] 非対称ジルコナシクロペンタジエンの選択的プロトン化/ヨウ素化反応によるモノヨードブタジエン誘導体の合成 (2010)
  • Author(s): 五十嵐絵里・任申勇・菅野研一郎・高橋保
  • Organizer: 第90日本化学会春季年会
  • Place of Presentation: 大阪市
  • Year and Date: 2010-03-27
• [Presentation] 非対称ジルコナシクロペンタジエンの選択的プロトン化/ヨウ素化反応によるモノヨードブタジエン誘導体の合成 (2010)
  • Author(s): 五十嵐絵里・任申勇・菅野研一郎・高橋保
  • Organizer: 90日本化学会春季年会
  • Place of Presentation: 大阪市, 近畿大学
  • Year and Date: 2010-03-27
• [Presentation] Linear Triene and Tetraene Formation via Selective Coupling Reaction of Three and Four Different Alkynes Using Zirconocene CRC International Symposium on Innovation Driven by Catalysis-past, present and future (2009)
  • Author(s): E.Igarashi, K.Kanno, L.Zhou, K.Nakajima, T.Takahashi
  • Place of Presentation: 札幌市
  • Year and Date: 2009-12-08
• [Presentation] Linear Triene and Tetraene Formation via Selective Coupling Reaction of Three and Four Different Alkynes Using Zirconocene (2009)
  • Author(s): E.Igarashi, K.Kanno, L.Zhou, K.Nakajima, T.Takahashi
  • Organizer: CRC International Symposium on "Innovation Driven by Catalysis-past, present and future"
  • Place of Presentation: 札幌市, 北海道大学
  • Year and Date: 2009-12-08
• [Presentation] 置換ヘプタトリエン誘導体のカルボリチオ化による7-endo-trig型環化反応 (2009)
  • Author(s): 五十嵐絵里、任申勇、中島清彦、菅野研一郎、高橋保
  • Organizer: 第56回有機金属化学討論会
  • Place of Presentation: 京都市
  • Year and Date: 2009-09-11
• [Presentation] 置換ヘプタトリエン誘導体のカルボリチオ化による7-endo-trig 型環化反応 (2009)
  • Author(s): 五十嵐絵里、任申勇、中島清彦、菅野研一郎、高橋保
  • Organizer: 第56回有機金属化学討論会
  • Place of Presentation: 京都市, 同志社大学
  • Year and Date: 2009-09-11
• [Presentation] Selective Linear Triene and Tetraene Formation from Three or Four Different Alkynes Using Zirconocene (2008)
  • Author(s): Igarashi, E.; Kanno, K.; Zhou, L.; Nakajima, K.; Takahashi, T.
  • Organizer: The 60th Southeastern Regional Meeting of American Chemical Society (SERMACS 2008)
  • Place of Presentation: ナッシュビル(アメリカ)
  • Year and Date: 2008-11-12
• [Presentation] Selective Linear Triene and Tetraene Formation from Three or Four Different Alkvnes Usine Zirconocene (2008)
  • Author(s): Igarashi, E. ; Kanno, K. ; Thou, L. ; N akajima, K. ; Takahashi, T.
  • Organizer: The 60th Southeastern Regional Meeting of American Chemical Society (SERMACS 2008)
  • Place of Presentation: ナッシュビル(アメリカ)
  • Year and Date: 2008-11-12
• [Presentation] ジルコナサイクルを経由するアルキンの直鎖状多量化反応 (2008)
  • Author(s): 五十嵐絵里・菅野研一郎・周立山・中島清彦・高橋保
  • Organizer: 第55回有機金属化学討論会
  • Place of Presentation: 大阪市
  • Year and Date: 2008-09-29
• [Presentation] ジルコノセン錯体を用いた2種のアルキンと求電子剤との3成分カップリング反応 (2008)
  • Author(s): 五十嵐絵里、周立山、中島清彦、菅野研一郎、高橋保
  • Organizer: 2008年日本化学会北海道支部夏季研究発表会
  • Place of Presentation: 北見市
  • Year and Date: 2008-07-19
• [Presentation] Linear Triene and Tetraene Formation via Selective Alkyne Coupling Using Zirconocene Complexes (2008)
  • Author(s): E.Igarashi, K.Kanno, L.Zhou, K.Nakajima, T.Takahashi
  • Organizer: the 23rd International Conference on Organometallic Chemistry (ICOMC2008)
  • Place of Presentation: レンヌ(フランス)
  • Year and Date: 2008-07-14
• [Presentation] Selective Linear Triene and Tetraene Formation from Three or Four Different Alkynes Using Zirconocene (2008)
  • Author(s): Igarashi, E.; Kanno, K.; Zhou, L.; Nakajima, K.; Takahashi, T.
  • Organizer: Taiwan-Japan International Symposium on Organic Chemistry and Molecular Science
  • Place of Presentation: 台北(台湾)
  • Year and Date: 2008-04-19