Synthetic Method for Non-planar Polyaromatic Hydorocarbon Based on Carbon-Hydrogen Bond Cleavage Reaction

• Project/Area Number: 20550048
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Organic chemistry
• Research Institution: Osaka Prefecture University
• Principal Investigator: KEN Kamikawa Osaka Prefecture University, 理学系研究科, 准教授 (40316021)
• Project Period (FY): 2008 – 2010
• Project Status: Completed (Fiscal Year 2010)
• Budget Amount: ¥4,940,000 (Direct Cost: ¥3,800,000、Indirect Cost: ¥1,140,000); Fiscal Year 2010: ¥1,430,000 (Direct Cost: ¥1,100,000、Indirect Cost: ¥330,000); Fiscal Year 2009: ¥1,560,000 (Direct Cost: ¥1,200,000、Indirect Cost: ¥360,000); Fiscal Year 2008: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000)
• Keywords: 反応有機化学 / C-H活性化 / ヘリセン / フラーレン

Research Abstract

We have succeeded synthesis of non-planar polyaromatic hydrocarbon such as helicene and benzoacenaphthylene by utilizing palladium catalyzed direct C-H arylation reactions. These synthetic methodologies gave short steps synthesis without any preactivation of the substrate. The studies of fluorecene in acenaphtylene derivatives were also achieved.

Research Products

• [Journal Article] Induction of Axially Chiral N-C Bond in N-Aryl Acidane by Stereoselective Chromium Tricarbonyl Migration (2010)
  • Author(s): Mori, A.; Kinoshita, S.; Furusyo, M.; Kamikawa, K.
  • Journal Title: Chem.Commun. Vol.46 Pages: 6846-6848
  • Peer Reviewed
• [Journal Article] Molecular Design of Small Organic Molecules Based on Structural Infomation for a Confomationally Constrained Peptide that Binds to G-CSF Receptor (2010)
  • Author(s): El-Haggar, R.; Kamikawa, K.; Machi, K.; Ye, Z.; Ishino, Y.; Tsumuraya, Fujii, I.
  • Journal Title: Bioorg.Med.Chem.Lett. Vol.20 Pages: 1169-1172
  • Peer Reviewed
• [Journal Article] Molecular Design of Small Organic Molecules Based on Structural Information for a Conformationally Constrained Peptide that Binds to G-CSF Receptor (2010)
  • Author(s): El-Haggar, R.; Kamikawa, K.; Machi, K.; Ye, Z.; Ishino, Y.; Tsumuraya, Fujii, I.
  • Journal Title: Bioorg.Med.Chem.Lett. Volume: 20 Pages: 1169-1172
  • Peer Reviewed
• [Journal Article] Induction of Axially Chiral N-C Bond in N-Aryl Acridane by Stereoselective Chromium Tricarbonyl Migration (2010)
  • Author(s): Mori, A.; Kinoshita, S.; Furusyo, M.; Kamikawa, K.
  • Journal Title: Chem.Commun. Volume: 46 Pages: 6846-6848
  • Peer Reviewed
• [Journal Article] Induction of one-handed helical oligo(p-benzammide)s by domino effect based on planar-axial-helical chirality relay (2010)
  • Author(s): El-Haggar, R.; Kamikawa, K.; Machi, K.; Ye, Z.; Ishino, Y.; Tsumuraya, Fujii, I.
  • Journal Title: Bioorg.Med.Chem.Lett. 20 Pages: 1169-1172
  • Peer Reviewed
• [Journal Article] Synthesis of Organocatalysts with One-handed Helix and Their Application to the Kinetic Resolution of Secondary Alcohol (2009)
  • Author(s): Kamikawa, K.; Shiromoto, T.; Yamaguchi, J. Takemoto, S.; Matsuzaka, H.
  • Journal Title: Res.Chem.Intermed. Vol.35 Pages: 1201-1203
  • Peer Reviewed
• [Journal Article] Induction of One-handed Helical Oligo (p-benzammide) s by Domino Effect Based on Planar-axial-helical Chirality Relay (2009)
  • Author(s): Kamikawa, K.; Kinoshita, S.; Furusyo, M.; Takemoto, S.; Matsuzaka, H.; Uemura, M.
  • Journal Title: Chem.Commun. Pages: 1201-1203
  • Peer Reviewed
• [Journal Article] Synthesis of Organocatalysts with One-handed Helix and Their Application to the Kinetic Resolution of Secondary Alcohol (2009)
  • Author(s): Kamikawa, K.; Shiromoto, T.; Yamaguchi, J.Takemoto, S.; Matsuzaka, H.
  • Journal Title: Res.Chem.Intermed. 35 Pages: 931-937
  • Peer Reviewed
• [Journal Article] Induction of one-handed helical oligo(p-benzammide)s by domino effect based on planar-axial-helical chirality relay (2009)
  • Author(s): Kamikawa, K., Kinoshita, S., Furusyo, M., Takemoto, S., Matsuzaka, H., Uemura, M.
  • Journal Title: Chem. Commun. Pages: 1201-1203
  • Peer Reviewed
• [Journal Article] Asymmetric Synthesis of Axially Chiral Compound Utilizing Planar Chiral Transition Metal Complexes and Their Development for Dynamic Complexes (2008)
  • Author(s): Kamikawa, K.
  • Journal Title: J.Synth.Org.Chem.Jpn. Vol.66 Pages: 953-964
  • NAID: 10024329019
  • Peer Reviewed
• [Journal Article] Asymmetric Synthesis of Axially Chiral Compound Utilizing Planar Chiral Transition Metal Complexes and Their Development for Dynamic Complexes (2008)
  • Author(s): Kamikawa, K.
  • Journal Title: J. Synth. Org. Chenm. Jpn. 66 Pages: 953-964
  • NAID: 10024329019
  • Peer Reviewed
• [Journal Article]
  • Author(s): Ogasawara, M.; Wu, W.-Y.; Arae, S.; Morita, T.; Watanabe, S.; Takahashi, T.; Kamikawa, K.J.
  • Journal Title: Organomet.Chem. in press
  • Peer Reviewed
• [Presentation] モリブデン触媒不斉閉環メタセシスによる面不斉アレーンクロム錯体の速度論分割 (2011)
  • Author(s): 小笠原正道, 呉威毅, 神川憲, 渡邊進, 荒江祥永, 高橋保
  • Organizer: 日本化学会第91春季年会 日本化学会第91春季年会(2011)講演予稿集
  • Year and Date: 2011-03-11
• [Presentation] モリブデン触媒不斉閉環メタセシスによる面不斉アレーンクロム錯体の速度論分割 (2011)
  • Author(s): 小笠原正道, 呉威毅, 神川憲, 渡邊進, 荒江祥永, 高橋保
  • Organizer: 日本化学会第91春季年会
  • Place of Presentation: 日本化学会第91春季年会(2011)講演予稿集
  • Year and Date: 2011-03-11
• [Presentation] Induction of one-handed helical oligo (p-benzamide) s by domino effect based on planar-axial-helical chirality relay (2010)
  • Author(s): J. Yamaguchi, K.Kamikawa
  • Organizer: Pacifichem 2010
  • Place of Presentation: 米国ハワイ
  • Year and Date: 2010-12-17
• [Presentation] Induction of one-handed helical oligo(p-benzamide)s by domino effect based on planar-axial-helical chirality relay (2010)
  • Author(s): J.Yamaguchi, K.Kamikawa
  • Organizer: Pacifichem 2010
  • Place of Presentation: 米国 ハワイ
  • Year and Date: 2010-12-17
• [Presentation] Induction of Axially Chiral N-C Bond in N-Aryl Acridane by Stereoselective Chromium Tricarbonyl Migration (2010)
  • Author(s): A. Mori, S. Kinoshita, K.Kamikawa
  • Organizer: Pacifichem 2010
  • Place of Presentation: 米国ハワイ
  • Year and Date: 2010-12-16
• [Presentation] Induction of Axially Chiral N-C Bond in N-Aryl Acridane by Stereoselective Chromium Tricarbonyl Migration (2010)
  • Author(s): A.Mori, S.Kinoshita, K.Kamikawa
  • Organizer: Pacifichem 2010
  • Place of Presentation: 米国 ハワイ
  • Year and Date: 2010-12-16
• [Presentation] クロムトリカルボニル基の移動によるN-アリールアクリダン類のC-N軸不斉誘導 (2010)
  • Author(s): 神川憲、森明義
  • Organizer: 有機金属化学討論会
  • Place of Presentation: 東京都中央大学
  • Year and Date: 2010-09-17
• [Presentation] クロムトリカルボニル基の移動によるN-アリールアクリダン類のC-N軸不斉誘導 (2010)
  • Author(s): 神川憲、森明義、神川憲
  • Organizer: 有機金属化学討論会
  • Place of Presentation: 東京都 中央大学
  • Year and Date: 2010-09-17
• [Presentation] Pd触媒を用いたビナフチルハライドとアルキンとの環化付加反応 (2010)
  • Author(s): 神川憲、石坂友香
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪・近畿大学
  • Year and Date: 2010-03-29
• [Presentation] 立体選択的面不斉移動を活用したN-アリールアクリダン塁のC-N軸不斉誘導 (2010)
  • Author(s): 神川憲、森明義
  • Organizer: 日本化学会第90春季年会
  • Place of Presentation: 大阪・近畿大学
  • Year and Date: 2010-03-28
• [Presentation] 軸不斉および高次不斉構造化合物の新合成戦略 (2010)
  • Author(s): 神川憲
  • Organizer: ヘテロ原子部会平成21年度第3回懇話会
  • Place of Presentation: 大阪・大阪科学技術センター
  • Year and Date: 2010-02-12
• [Presentation] 動的分子を活用した立体選択的合成及び構造制御 (2009)
  • Author(s): 神川憲
  • Organizer: 京都大学薬学研究科講演
  • Place of Presentation: 京都・京都大学
  • Year and Date: 2009-11-25
• [Presentation] キラルリレーに基づくドミノ効果を活用したオリゴベンズアミドのらせん不斉制御 (2009)
  • Author(s): 神川憲
  • Organizer: 「炭素資源の高度分子変換」取り纏めシンポジウム
  • Place of Presentation: 京都・京都テルサ
  • Year and Date: 2009-06-01
• [Presentation] 動的分子を活用した立体選択的反応および構造制御 (2009)
  • Author(s): 神川憲
  • Organizer: 有機金属部会平成21年度第3回例会
  • Place of Presentation: 岡山・岡山大学
  • Year and Date: 2009-06-01
• [Presentation] Stereoselective Synthesis of Axially Chiral Biaryl Compounds by Planar Chiral Transition Metal Complexes (2009)
  • Author(s): 神川憲
  • Organizer: Second Japan-Singapore Bilateral Symposium on Catalysis
  • Place of Presentation: Kyoto
  • Year and Date: 2009-01-05
• [Book] 使える!有機合成反応実践ガイド (2010)
  • Author(s): 化学同人、丸岡啓二、野崎京子、石井康敬、大寺純蔵、富岡清編著
• [Book] 天然物の全合成 (2009)
  • Author(s): 化学同人、有機合成化学協会編、共著
  • Total Pages: 103
• [Remarks] ホームページ
  • URL: http://www.c.s.osakafu-u.ac.jp/~kamikawa/index.html