New synthesis of organofluorine compounds using fluorinated carbenes and their derivatives

• Project/Area Number: 18350054
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Single-year Grants
• Section: 一般
• Research Field: Synthetic chemistry
• Research Institution: Kobe University
• Principal Investigator: AMII Hideki Kobe University, 大学院・理学研究科, 准教授 (00284084)
• Co-Investigator(Kenkyū-buntansha): HAYASHI Masahiko 神戸大学, 大学院・理学研究科, 教授 (60192704)
• Project Period (FY): 2006 – 2008
• Project Status: Completed (Fiscal Year 2008)
• Budget Amount: ¥17,120,000 (Direct Cost: ¥15,800,000、Indirect Cost: ¥1,320,000); Fiscal Year 2008: ¥1,950,000 (Direct Cost: ¥1,500,000、Indirect Cost: ¥450,000); Fiscal Year 2007: ¥3,770,000 (Direct Cost: ¥2,900,000、Indirect Cost: ¥870,000); Fiscal Year 2006: ¥11,400,000 (Direct Cost: ¥11,400,000)
• Keywords: 有機合成化学 / 有機フッ素化合物 / 有機金属化学 / 選択的変換 / カルベン

Research Abstract

本研究は、有機フッ素化合物の新しい合成ルートの開発を行なうものである。
有機フッ素化合物は、フッ素原子の醸し出す種々の興味深い特性により、医薬農薬並びに材料等の広い分野への応用が注目されている。本研究において、含フッ素カルベン、含フッ素アルキル金属種などの含フッ素活性種を用い、新たにジフルオロメチレン化合物およびトリフルオロメチル化合物の効率的合成法を開発することに成功した。

Research Products

• [Journal Article] Aromatic Trifluoromethylation Catalytic in Copper (2009)
  • Author(s): Oishi, M.; Kondo, H.; Amii. H.
  • Journal Title: Chem.Commun 14 Pages: 1909-1911
• [Journal Article] C-F Bond Activation in Organic Synthesis (2009)
  • Author(s): Amii, H.; Uneyama, K.
  • Journal Title: Chem.Rev. 109(5) Pages: 2119-2183
• [Journal Article] Aromatic Trifluoromethylation Catalytic in Copper (2009)
  • Author(s): Masahiro Oishi
  • Journal Title: Chemical Communications 第14号 Pages: 1909-1911
  • Peer Reviewed
• [Journal Article] C-F Bond Activation in Organic Synthesis (2009)
  • Author(s): Hideki Amii
  • Journal Title: Chemical Reviews 第109巻(印刷中)
  • Peer Reviewed
• [Journal Article] Selective Aromatic Carbon-Oxygen Bond Cleavage of Trifluoromethoxyarenes : A Trifluoromethoxy Group as a Convertible Directing Group (2008)
  • Author(s): Iijima, A.; Amii. H.
  • Journal Title: Tetrahedron Lett. 49(41) Pages: 6013-6015
• [Journal Article] α-Trifluoromethylated Carbanion Synthons (2008)
  • Author(s): Uneyama, K.; Katagiri, T.; Amii. H.
  • Journal Title: Ace.Chem.Res. 41(7) Pages: 817-829
• [Journal Article] Boron-Substituted Difluorocyclopropanes : New Building Blocks of gem-Difluorocyclopropanes (2008)
  • Author(s): Fujioka, Y.; Amfi, H.
  • Journal Title: Org.Lett. 10(5) Pages: 769-772
• [Journal Article] Selective Aromatic Carbon-Oxygen Bond Cleavage of Trifluoromethoxyarenes : A Trifluoromethoxy Group as a Convertible Directing Group (2008)
  • Author(s): Akinori Iijima
  • Journal Title: Tetrahedron Letters 第49巻第41号 Pages: 6013-6015
  • Peer Reviewed
• [Journal Article] Boron-Substituted Difluorocyclopropanes: New Building Blocks of gem-Difluorocyclopropanes (2008)
  • Author(s): Yasutaka Fujioka
  • Journal Title: Organic Letters 第10巻第5号 Pages: 769-772
  • Peer Reviewed
• [Journal Article] Selective Defluorination Approach to N-Cbz-3, 3-difluoro-2-difluoromethylenepyrrole and Its Application to 3, 3-Difluoroproline Dipeptide Synthesis (2007)
  • Author(s): Guo, Y.; Fujiwara, K.; Amii. H.; Uneyama, K.
  • Journal Title: J.Org.Chem. 72(22) Pages: 8523-8526
• [Journal Article] Selective Defluorination Approach to N-Cbz-3, 3-difluoro-2-difluoromethylenepyrrole and Its Application to 3, 3-DifluoroproIine Dipeptide Synthesis (2007)
  • Author(s): Guo Yong
  • Journal Title: The Journal of Organic Chemistry 第72巻第22号 Pages: 8523-8526
  • Peer Reviewed
• [Presentation] ヘテロ環化合物へのトリフルオロメチル基の触媒的導入 (2009)
  • Author(s): 近藤秀昭・大石真弘・網井秀樹一
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学理工学部船橋キャンパス
  • Year and Date: 2009-03-30
• [Presentation] アルコール部位を持つ軸不斉ホスフィン配位子の合成と応用 (2009)
  • Author(s): 森川悟史・網井秀樹
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学理工学部船橋キャンパス
  • Year and Date: 2009-03-28
• [Presentation] 新しい軸不斉有機分子触媒合成とその応用 (2009)
  • Author(s): 道上恭佑・森川悟史・網井秀樹
  • Organizer: 日本化学会第89春季年会
  • Place of Presentation: 日本大学理工学部船橋キャンパス
  • Year and Date: 2009-03-27
• [Presentation] Selective Activation of C-F and C-O Bonds for Organic Synthesis (2009)
  • Author(s): Hideki Amii
  • Organizer: Research Colloquium in Universite Paris Diderot (Paris 7)
  • Place of Presentation: Paris, France
  • Year and Date: 2009-03-18
• [Presentation] 含フッ素官能基導入法の開発と応用 (2008)
  • Author(s): 網井秀樹
  • Organizer: グローバルCOE「統合物質科学」セミナー
  • Place of Presentation: 京都大学桂キャンパス
  • Year and Date: 2008-12-13
• [Presentation] 遷移金属触媒を用いたケイ素置換フランの位置選択的合成 (2008)
  • Author(s): 早川修平・網井秀樹
  • Organizer: 第28回有機合成若手セミナー
  • Place of Presentation: 大阪大学
  • Year and Date: 2008-11-12
• [Presentation] Aromatic Trifluoromethylation Catalytic in Copper (2008)
  • Author(s): Masahiro Oishi, Hideaki Kondo, Hideki Amii
  • Organizer: The Fifth International Symposium on Integrated Synthesis (ISIS-5)
  • Place of Presentation: Kobe
  • Year and Date: 2008-09-06
• [Presentation] 新しいジフルオロシクロプロパン合成ブロックの創製とその応用 (2008)
  • Author(s): 網井秀樹
  • Organizer: 第15回有機フッ素化学化学セミナー
  • Place of Presentation: 岡山大学
  • Year and Date: 2008-08-30
• [Presentation] Synthesis and Application of Boryl- and Silyl-Substituted Difluoroyclopropanes (2008)
  • Author(s): Yoshimichi Morimoto, Yasutaka Fujioka, Hideki Amii
  • Organizer: XXIII International Conference on Organometallic Chemistry (ICOMC 2008)
  • Place of Presentation: Rennes
  • Year and Date: 2008-07-17
• [Presentation] Synthesis and Application of Boryl- and Silyl-Substituted Difluoroyclopropanes. (2008)
  • Author(s): Yoshimichi Morimoto
  • Organizer: XXIII International Conference on Organometallic Chemistry
  • Place of Presentation: Rennes, France
  • Year and Date: 2008-07-17
• [Presentation] 触媒的トリフルオロメチル基導入反応の開発 (2008)
  • Author(s): 大石真弘・網井秀樹
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 立教大学
  • Year and Date: 2008-03-26
• [Presentation] 触媒的トリフルオロメチル基導入反応の開発 (2008)
  • Author(s): 大石真弘
  • Organizer: 日本化学会第88春季年会
  • Place of Presentation: 東京
  • Year and Date: 2008-03-26
• [Presentation] ジフルオロメチレン基、トリフルオロメチル基の入れ方と使い方 (2007)
  • Author(s): 網井秀樹
  • Organizer: 第四回有機元素化学セミナー
  • Place of Presentation: 京都大学宇治キャンパス
  • Year and Date: 2007-11-20
• [Presentation] Synthesis and Applications of Boryl-Substituted Difluorocyclopropanes (2007)
  • Author(s): Yasutaka Fujioka, Hideki Amii
  • Organizer: 14th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis (OMCOS 14)
  • Place of Presentation: Nara
  • Year and Date: 2007-08-03
• [Presentation] Synthesis and Applications of Boryl-Substituted Difluorocyclopropanes (2007)
  • Author(s): Yasutaka Fujioka
  • Organizer: 14th IUPAC International Symposium on Organometallic Chemistry Directed Towards Organic Synthesis
  • Place of Presentation: 奈良
  • Year and Date: 2007-08-03
• [Presentation] 官能基を有するジフルオロシクロプロパンの合成化学的応用 (2007)
  • Author(s): 森本佳道・藤岡恭丘・網井秀樹
  • Organizer: 日本化学会第87春季年会
  • Place of Presentation: 関西大学
  • Year and Date: 2007-03-28
• [Presentation] Selective C-O Bond Functionalization of Trifluoromethoxybenzene (2006)
  • Author(s): Akinori Iijima, Hideki Amii
  • Organizer: The 10th International Kyoto Conference on New Aspect of Organic Chemistry (IKCOC-10)
  • Place of Presentation: Kyoto
  • Year and Date: 2006-11-14
• [Presentation] ホウ素化ジフルオロシクロプロパンの合成とその応用 (2006)
  • Author(s): 藤岡恭丘・網井秀樹
  • Organizer: 第30回フッ素化学討論会
  • Place of Presentation: 鳥取
  • Year and Date: 2006-11-09
• [Patent(Industrial Property Rights)] 網井秀樹・大城幸純・森本佳道・松浦誠 (2010)
  • Inventor(s): ジフルオロシクロプロパン化合物の製造方法
  • Industrial Property Number: 2010-003201
  • Filing Date: 2010-01-08
• [Patent(Industrial Property Rights)] 網井秀樹・藤川憲一・藤岡恭丘・松浦誠 (2009)
  • Inventor(s): 芳香族ジフルオロメチル化合物の製造方法
  • Industrial Property Number: 2009-263315
  • Filing Date: 2009-11-18
• [Patent(Industrial Property Rights)] 網井秀樹・藤川憲一・藤岡恭丘・松浦誠 (2009)
  • Inventor(s): 芳香族ジフルオロ酢酸エステルの製造方法
  • Industrial Property Number: 2009-263316
  • Filing Date: 2009-11-18