文部科学省 新学術領域研究(平成27年~31年)高難度物質変換反応の開発を指向した精密制御反応場の創出

柴田 哲男 » English

所属 名古屋工業大学大学院工学研究科
役職 教授
連絡先 Email
HP http://www.ach.nitech.ac.jp/~organic/shibata/index.html
専門分野 化学、有機フッ素化学、創薬化学
研究キーワード フッ素、サブフタロシアニン、フタロシアニン、トリフルオロメチル化、光反応
所属学会・研究会 日本化学会、 日本薬学会、 有機合成化学協会、 日本フッ素化学会、米国化学会

概要

当該研究では,1.フッ素化サブフタロシアニンが創るお椀型のπ電子空間の性質を調べ,2.そのπ電子空間と相互作用する有機分子を探し出し,3.最終的には,その空間を利用した特異な反応を開発することを目的とする。既にトリフルオロエトキシ化サブフタロシアニンが持つ分子包括特性の予備研究を行っており,フッ素が持つ強力な脂溶性および電子求引性が重要であることがわかってきた。さらにサブフタロシアニンは光触媒としての機能を有することもわかってきており,LED等の光照射下での反応等を計画している。

研究業績

印刷用ページを開く

原著論文

  • "Trifluoroethoxy-Coated Subphthalocyanine affects Trifluoromethylation of Alkenes and Alkynes even under Low-Energy Red-Light Irradiation"
    Matsuzaki, K.; Hiromura, T.; Tokunaga, E.; Shibata, N.
    ChemistryOpen, 2017, 6, 226-230
  • "Synthesis and Optical Properties of Fluorine-Containing Phthalocyanine Conjugated with Glucofuranose and its Application to Photo-Dynamic Therapy"
    Mori, S.; Tokunaga, E.; Hayashi, M.; Obata, T.; Tanaka, M.; Shibata, N.
    J. Jpn. Soc. Colour Mater., 2016, 89(7), 213-218
  • "Design, synthesis and optical properties of unsymmetrical subphthalocyanine trimer connected by phloroglucinol via axial positions"
    Mori, S.; Ogawa, N.; Tokunaga, E.; Tsuzuki, S.; Shibata, N.
    Dalton Trans., 2016, 45, 908-912
  • "Successive C–C bond cleavage, fluorination, trifluoromethylthio- and pentafluorophenylthiolation under metal-free conditions to provide compounds with dual fluoro-functionalization"
    Saidalimu, I.; Suzuki, S.; Tokunaga, E.; Shibata, N.
    Chem. Sci., 2016, 7, 2106-2110
  • "Activation of Trifluoromethylthio Moiety by Appending Iodonium Ylide under Copper Catalysis for Electrophilic Trifluoromethylation Reaction"
    Saidalimu, I.; Suzuki, S.; Tokunaga, E.; Shibata, N.
    Chin. J. Chem., 2016, 34, 485-489
  • "Enantioselective Trichloromethylation of MBH-Fluorides with Chloroform Based on Silicon-assisted C-F Activation and Carbanion Exchange Induced by a Ruppert-Prakash Reagent"
    Nishimine, T.; Taira, H.; Tokunaga, E.; Shiro, M.; Shibata, N.
    Angew. Chem., Int. Ed., 2016, 55(1), 359-363
  • "Methyl NFSI: atom-economical alternative to NFSI shows higher fluorination reactivity under Lewis acid-catalysis and non-catalysis"
    Fukushi, K.; Suzuki, S.; Kamo, T.; Tokunaga, E.; Sumii, Y.; Kagawa, T.; Kawada, K.; Shibata, N.
    Green Chem., 2016, 18, 1864-1868
  • "2-Diazo-1-phenyl-2-((trifluoromethyl)sulfonyl)ethan-1-one: Another Utility for Electrophilic Trifluoromethylthiolation Reactions"
    Huang, Z.; Okuyama, K.; Wang, C.; Tokunaga, E.; Li, X.; Shibata, N.
    ChemistryOpen, 2016, 5, 188-191
  • "Lewis Acid-Catalyzed Selective Mono-fluorination of Malonates Using Me-NFSI"
    Fukushi, K.; Tokunaga, E.; Sumii, Y.; Kagawa, T.; Nagasaki, N.; Shibata, N.
    Fluorine notes, 2016, 105, 2
  • "Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene-ynes"
    Okusu, S.; Okazaki, H.; Tokunaga, E.; Soloshonok, V. A.; Shibata, N.
    Angew. Chem., Int. Ed., 2016, 55, 6744-6748
  • "Copper-Catalyzed Regioselective Trifluoromethylthiolation of Pyrroles by Trifluoromethanesulfonyl Hypervalent Iodonium Ylide"
    Huang, Z.; Yang, Y.-D.; Tokunaga, E.; Shibata, N.
    Org. Lett., 2015, 17(5), 1094-1097
  • "Trifluoromethylthiolation of Allylsilanes and Silyl Enol Ethers with Trifluoromethanesulfonyl Hypervalent Iodonium Ylide under Copper Catalysis"
    Arimori, S.; Takada, M.; Shibata, N.
    Org. Lett. , 2015, 17(5), 1063-1065
  • "Carbene-Induced Intra- vs Intermolecular Transfer-Fluoromethylation of Aryl Fluoromethylthio Compounds under Rhodium Catalysis"
    Saidalimu, I.; Tokunaga, E.; Shibata, N.
    ACS Catal., 2015, 5(8), 4668?4672
  • "Synthesis and optical properties of subphthalocyanine homo- and heterodimers axially connected via a hydroquinone linker"
    Mori, S.; Ogawa, N.; Tokunaga, E.; Shibata, N.
    Dalton Trans., 2015, 44, 19451-19455
  • "Synthesis of Phthalocyanines with a Pentafluorosulfanyl Substituent at Peripheral Positions"
    Iida, N.; Tanaka, K.; Tokunaga, E.; Mori, S.; Saito, N.; Shibata, N.
    ChemistryOpen, 2015, 4(6), 698-702
  • "Stereoselective Synthesis of β-Lactam-triflones under Catalyst-Free Conditions"
    Huang, Z.; Wang, C.; Tokunaga, E.; Sumii, Y.; Shibata, N.
    Org. Lett., 2015, 17(22), 5610-5613
  • "Design, synthesis and optical properties of unsymmetrical subphthalocyanine trimer connected by phloroglucinol via axial positions"
    Mori, S.; Ogawa, N.; Tokunaga, E.; Tsuzuki, S.; Shibata, N.
    Dalton Trans., 2015, 45, 908-912
  • "Successive C-C bond cleavage, fluorination, trifluoromethylthio- and pentafluorophenylthiolation under metal-free conditions to provide compounds with dual fluoro-functionalization"
    Saidalimu, I.; Suzuki, S.; Tokunaga, E.; Shibata, N.
    Chem. Sci., 2015, 7, 2106-2110
  • "Regioisomer-Free C4h β-Tetrakis(tert-butyl)metallo-phthalocyanines: Regioselective Synthesis and Spectral Investigations"
    Iida, N.; Tanaka, K.; Tokunaga, E.; Takahashi, H.; Shibata, N.
    ChemistryOpen, 2014, 4(2), 102-106
  • "Synthesis and optical properties of trifluoroethoxy-substituted double-decker phthalocyanines"
    Mori, S.; Ogawa, N.; Tokunaga, E.; Shibata, N.
    J. Porphyrins Phthalocyanines, 2014, 18, 1034
  • "Design, synthesis, spectral investigations and biological activity of fluorinated phthalocyanine conjugated with galactose and comparison to its non-fluorinated counterpart"
    Mori, S.; Yoshiyama, H.; Tokunaga, E.; Iida, N.; Hayashi, M.; Obata, T.; Tanaka M.; Shibata, N.
    J. Fluorine Chem., 2014, 174, 137-141

著書

  • 「Development of Shelf-Stable Reagents for Electrophilic Trifluoromethylthiolation Reaction」
    Huang, Z.; Shibata, N.
    「New Horizons of Process Chemistry」, Springer, 2017

総説・解説

  • 「Development of Shelf-Stable Reagents for Fluoro-Functionalization Reactions」 Shibata, N., Bull. Chem. Soc. Jpn., 89, 1307-1320, 2016