Metal-catalyzed cross-coupling reaction between aryl and fluorofunctional groups by using strong electron-poor ligand

• Project/Area Number: 20550099
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Okayama University
• Principal Investigator: KORENAGA Toshinobu Okayama University, 大学院・自然科学研究科, 助教 (70335579)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2009: ¥1,820,000 (Direct Cost: ¥1,400,000、Indirect Cost: ¥420,000); Fiscal Year 2008: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000)
• Keywords: 芳香族フッ素化合物 / クロスカップリング / 還元的脱離反応 / 電子不足配位子 / 電子的効果 / DFT計算 / 含フッ素配位子 / ジボスフィン / 配位子効果 / ジホスフィン / 反結合性軌道 / 分子軌道計算 / 還元的脱離 / 支持配位子 / ホスフィン / クロスカップリング反応 / トリフルオロメチル基 / フッ素化芳香環

Research Abstract

Metal-catalyzed coupling reaction between aryl and fluorofunctional group was studied. Firstly, we investigated the electronic effect of supporting ligand on reductive elimination of biaryl. As a result, we found that the strong electron-poor diphosphine ligand accelerated reductive elimination of biaryl. Secondly, we tried the reductive elimination of aryl and fluorofunctional group from palladium catalyst bearing strong electron-poor ligand. However, the complex was decomposed before reductive elimination at high reaction temperature.

Research Products

• [Journal Article] Ligand Electronic Effect on Reductive Elimination of Biphenyl from Cis-[Pt(Ph)_2(diphosphine)] Complexes Bearing Electron-poor Diphosphine: Correlation Study Between Experimental and Theoretical Results (2010)
  • Author(s): Korenaga, T.; Abe, K.; Ko, A.; Maenishi, R.; Sakai, T.
  • Journal Title: Organometallics 29 Pages: 4025-4035
  • Peer Reviewed
• [Journal Article] Ligand Electronic Effect on Reductive Elimination of Biphenyl from Cis-[Pt(Ph)_2(diphosphine)] Complexes Bearing Electron-poor Diphosphine : Correlation Study Between Experimental and Theoretical Results (2010)
  • Author(s): Korenaga, T.; Abe, K; Ko, A; Maenishi, R.; Sakai, T.
  • Journal Title: Organometallics Volume: 29 Pages: 4025-4035
  • Peer Reviewed
• [Presentation] 酒井貴志白金ジフェニル錯体からの還元的脱離反応における含フッ素ジホスフィン配位子の加速効果 (2010)
  • Author(s): 是永敏伸, 阿部佳余子, コアラム, 依馬正
  • Organizer: 第34回フッ素化学討論会,講演要旨集62頁,講演番号O-27
  • Place of Presentation: 札幌
  • Year and Date: 2010-10-19
• [Presentation] 白金錯体からのビフェニルの還元的脱離における電子不足なジホスフィン配位子の電子的効果の解明 (2010)
  • Author(s): 是永敏伸, 阿部佳余子, コアラム, 依馬正, 酒井貴志
  • Organizer: 日本化学会第90春季年会,講演番号1B2-12
  • Place of Presentation: 大阪
  • Year and Date: 2010-03-26
• [Presentation] 含フッ素アリールホスフィン配位子による金属触媒反応加速効果 (2009)
  • Author(s): 是永敏伸
  • Organizer: 第16回有機フッ素化学セミナー
  • Place of Presentation: 岡山
  • Year and Date: 2009-09-12
• [Presentation] ジフェニル白金錯体の還元的脱離反応におけるジホスフィン配位子の電子的効果 (2009)
  • Author(s): 是永敏伸
  • Organizer: 第25回若手化学者のための化学道場
  • Place of Presentation: 松山
  • Year and Date: 2009-09-07
• [Presentation] Effect of Electron-poor Ligand on the Biaryl Reductive Elimination (2008)
  • Author(s): 是永敏伸, 阿部佳余子, 山川恭平, 依馬正, 酒井貴志
  • Organizer: 第55回有機金属化学討論会,講演要旨集9頁,講演番号O1-08
  • Place of Presentation: 大阪
  • Year and Date: 2008-09-28
• [Presentation] Effect of Electron-poor Ligand on the Biaryl Reductive Elimination (2008)
  • Author(s): 是永 敏伸, 阿部 佳余子, 山川 恭平, 依馬 正, 酒井 貴志
  • Organizer: 第55回有機金属化学討論会
  • Place of Presentation: 大阪
  • Year and Date: 2008-09-28