π空間を利用する有機分子フラスコ触媒の創成とトリフルオロメチル化反応の開発

• Project Area: Advanced Molecular Transformations by Organocatalysts
• Project/Area Number: 24105513
• Research Category: Grant-in-Aid for Scientific Research on Innovative Areas (Research in a proposed research area)
• Allocation Type: Single-year Grants
• Review Section: Science and Engineering
• Research Institution: Nagoya Institute of Technology
• Principal Investigator: 柴田 哲男 名古屋工業大学, 工学(系)研究科(研究院), 教授 (40293302)
• Project Period (FY): 2012-04-01 – 2014-03-31
• Project Status: Completed (Fiscal Year 2013)
• Budget Amount: ¥9,490,000 (Direct Cost: ¥7,300,000、Indirect Cost: ¥2,190,000); Fiscal Year 2013: ¥4,810,000 (Direct Cost: ¥3,700,000、Indirect Cost: ¥1,110,000); Fiscal Year 2012: ¥4,680,000 (Direct Cost: ¥3,600,000、Indirect Cost: ¥1,080,000)
• Keywords: 有機触媒 / π空間 / フッ素 / トリフルオロエトキシ / 不斉合成 / 生理活性物質 / 水素結合 / 光学活性 / 医薬品 / キナアルカロイド

Research Abstract

π空間触媒として想定するサブフタロシアニンが取り込む分子の一般性確認，及びフラスコの母体となる様々なサブフタロシアニン誘導体を用いたお椀構造内部への芳香族分子取り込み実験を行った。これまでの研究により，トリフルオロエトキシ化サブフタロシアニン内部にはトルエンとベンゼンが取り込まれることが明らかとなっている。これらの現象がトリフルオロエトキシ基によるものであることを確かめるため，無置換フタロシアニンとトリフルオロエトキシ基がアキシアル位で結合したダイマーを合成したところ，トリフルオロエトキシ化フタロシアニンのみにトルエンが取り込まれることがX線結晶構造解析により明らかとなり，トリフルオロエトキシ基の優位性が現れた。また環拡大型フラスコとして，トリフルオロエトキシ化フタロシアニンが一つのベンゼン環を介して連なったダイマーを合成した。本化合物はサブフタロシアニンモノマーより大きな化合物を取り込むためのフラスコとして利用できると考えられる。当初の目的である反応場としての応用の可能性が明確になったといえる。続いて，トリフルオロエトキシ化サブフタロシアニン自身の光触媒反応を検討することにした。光触媒として可視光域から近赤外域の光を吸収するルテニウム系色素が一般に使用されるが，ルテニウムは高価であるために，有機反応に用いるには問題がある。そこで，トリフルオロエトキシ化フタロシアニンを触媒に用いて，hex-5-en-1-olとペルフルオロオクチルヨージドをLEDランプの照射下にて行った。その結果，還元剤としてアルコルビン酸ナトリウムを用いることで，ラジカル付加反応が進行し，末端がペルフルオロアルキル化された化合物が77％で得られた。この結果は，トリフルオロエトキシ化サブフタロシアニンが光触媒として働いた初めての例である。上記両者を組み合わせたπ空間を利用する反応への展開が大いに期待出来る。

Current Status of Research Progress

Reason

25年度が最終年度であるため、記入しない。

Strategy for Future Research Activity

25年度が最終年度であるため、記入しない。

Research Products

• [Journal Article] Knetic Resolution of Allylic Fluorides by Enantioselective Allylic Trifluoromethylation based on Silicon-assisted C-F Bond Cleavage (2014)
  • Author(s): Takayuki Nishimine, Kazunobu Fukushi, Naoyuki Shibata, Hiromi Taira, Etsuko Tokunaga, Akihito Yamano, Motoo Shiro, Norio Shibata
  • Journal Title: Angewandte Chemie International Edition Volume: 53 Issue: 2 Pages: 517-520
  • DOI: 10.1002/anie.201308071
  • Peer Reviewed
• [Journal Article] S-((Phenylsulfonyl)difluoromethyl)thiophenium Salts: Carbon-Selective Electrophilic Difluoromethylation of β-Ketoesters, β-Diketones, and Dicyanoalkylidenes (2014)
  • Author(s): X. Wang, G. Liu, X.-H. Xu, N. Shibata, E. Tokunaga, N. Shibata
  • Journal Title: Angew. Chem. Int. Ed. Volume: 53 Issue: 7 Pages: 1827-1831
  • DOI: 10.1002/anie.201309875
  • Peer Reviewed
• [Journal Article] A phthalocyanine-subphthalocyanine heterodinuclear dimer: comparison of spectroscopic properties with those of homodinuclear dimers of constituting units (2014)
  • Author(s): N. Shibata, S. Mori, M. Hayashi, M. Umeda, E. Tokunaga, M. Shiro, H. Sato, T. Hoshi, N. Kobayashi
  • Journal Title: Chem. Comm. Volume: 50 Issue: 23 Pages: 3040-3043
  • DOI: 10.1039/c3cc49831j
  • Peer Reviewed / Open Access
• [Journal Article] Diastereoselective Additive Trifluoromethylation/Halogenation of Isoxazole Triflones: Synthesis of All-carbon Functionalized Trifluoromethyl Isoxazoline Triflones (2014)
  • Author(s): H. Kawai, Y. Sugita, E. Tokunaga, H. Sato, M. Shiro, N. Shibata
  • Journal Title: ChemistryOpen. Volume: 3 Issue: 1 Pages: 14-18
  • DOI: 10.1002/open.201300044
  • Peer Reviewed
• [Journal Article] Bis(pentafluorosulfanyl)phenyl Azide as an Expeditious Tool for Click Chemistry toward Antitumor Pharmaceuticals (2014)
  • Author(s): Y.-D. Yang, E. Tokunaga, H. Akiyama, N. Saito, N. Shibata
  • Journal Title: ChemMedChem Volume: in press Issue: 5 Pages: 913-917
  • DOI: 10.1002/cmdc.201400059
  • Peer Reviewed
• [Journal Article] Iodoarene-catalyzed fluorination and aminofluorination by Ar-I/HF・pyridine/mCPBA system (2014)
  • Author(s): Satoru Suzuki, Tomohiro Kamo, Kazunobu Fukushi, Takaaki Hiramatsu, Etsuko Tokunaga, Toshifumi Dohi, Yasuyuki Kita, Norio Shibata
  • Journal Title: Chemical Science Volume: 5 Issue: 7 Pages: 2754-2760
  • DOI: 10.1039/c3sc53107d
  • Peer Reviewed
• [Journal Article] Asymmetric Synthesis of Efavirenz via Organocatalyzed Enantioselective Trifluoromethylation (2014)
  • Author(s): S. Okusu, H. Kawai, Y. Yasuda, Y. Sugita, T. Kitayama, E. Tokunaga, N. Shibata
  • Journal Title: Asian J. Org. Chem. Volume: 3 Issue: 4 Pages: 449-452
  • DOI: 10.1002/ajoc.201402016
  • Peer Reviewed
• [Journal Article] A sterically demanding organo-superbase avoids decomposition of a naked trifluorometbyl carbanion directly generated from fluorofom (2013)
  • Author(s): Hiroyuki Kawai
  • Journal Title: Organic & Biomolecular Chemistry Volume: 11 Issue: 9 Pages: 1446-1550
  • DOI: 10.1039/c3ob27368g
  • Peer Reviewed
• [Journal Article] Enantioselective Synthesis of Epoxides Having a Tetrasubstituted Trifluoromethylated Carbon Center : Methylhydrazine-Induced Aerobic Epoxidation of β,β-Disubstituted Enones (2013)
  • Author(s): Hiroyuki Kawai
  • Journal Title: Angewandte Chemie International Edition Volume: 52 Issue: 8 Pages: 2221-2225
  • DOI: 10.1002/anie.201209355
  • Peer Reviewed
• [Journal Article] Efficient direct ester condensation between equimolar amounts of carboxylic acids and alcohols catalyzed by trifluoromethanesulfonic acid (TfOH) in Solkane365mfc (2013)
  • Author(s): X.-H. Xu, A. Azuma, M. Taniguchi, E. Tokunaga, N. Shibata
  • Journal Title: RSC Advances Volume: 3 Issue: 12 Pages: 3848-3852
  • DOI: 10.1039/c3ra00132f
  • Peer Reviewed
• [Journal Article] Cinchona Alkaloid/TMAF Combination : Enantioselective Trifluoromethylation of Aryl Aldehydes (2013)
  • Author(s): Hiroyuki Kawai
  • Journal Title: Journal of Fluorine Chemistry Volume: (in press) Pages: 46-50
  • DOI: 10.1016/j.jfluchem.2013.01.032
  • Peer Reviewed
• [Journal Article] Selective o-Difluoromethylation of 1,3-Diones by Bromodifluoromethylating Reagents (2013)
  • Author(s): G. Liu, X. Wang, X.-H. Xu, X. Lu, E. Tokunaga, S. Tsuzuki, N. Shibata
  • Journal Title: Org. Lett. Volume: 15 Issue: 5 Pages: 1044-1047
  • DOI: 10.1021/ol4000313
  • Peer Reviewed
• [Journal Article] Efficient Access to Trifluoromethyl Diarylpyrrolines and their N-Oxides through Enantioselective Conjugate Addition of Nitromethane to β, β-Disubstituted Enones (2013)
  • Author(s): H. Kawai, Z. Yuan, T. Kitayama, E. Tokunaga, N. Shibata
  • Journal Title: Angew. Chem. Int. Ed. Volume: 52 Issue: 21 Pages: 5575-5579
  • DOI: 10.1002/anie.201301123
  • Peer Reviewed
• [Journal Article] Highly Enantioselective Monofluoromethylation of C2-Arylindoles Using FBSM under Chiral Phase-Transfer Catalysis (2013)
  • Author(s): K. Matsuzaki, T. Furukawa, E. Tokunaga, T. Matsumoto, M. Shiro, N. Shibata
  • Journal Title: Org. Lett. Volume: 15 Issue: 13 Pages: 3282-3285
  • DOI: 10.1021/ol4013102
  • Peer Reviewed
• [Journal Article] Chiral N-Fluorodibenzenesulfonimide Analogues for Enantioselective Electrophilic Fluorination and Oxidative Fluorination (2013)
  • Author(s): C.-L. Zhu, M. Maeno, F.-G. Zhang, T. Shigehiro, T. Kagawa, K. Kawada, N. Shibata, J.-A. Ma, D. Cahard
  • Journal Title: Eur. J. Org. Chem. Volume: 2013 Issue: 29 Pages: 6501-6505
  • DOI: 10.1002/ejoc.201300956
  • Peer Reviewed
• [Journal Article] Enantioselective Synthesis of 5-Trifluoromethyl-2-isoxazolines and Their N-Oxides by [Hydroxy(tosyloxy)iodo]benzene-Mediated Oxidative N-O Coupling (2013)
  • Author(s): H. Kawai, S. Okusu, E. Tokunaga, N. Shibata
  • Journal Title: Eur. J. Org. Chem. Volume: 2013 Issue: 29 Pages: 6506-6509
  • DOI: 10.1002/ejoc.201301096
  • Peer Reviewed
• [Journal Article] Enantioselective monofluoromethylation of aldehydes with 2-fluoro-1,3-benzodithiole-1,1,3,3-tetraoxide catalyzed by a bifunctional cinchona alkaloid-derived thiourea-titanium complex (2013)
  • Author(s): H. Ma, K. Matsuzaki, Y.-D. Yang, E. Tokunaga, D. Nakane, T. Ozawa, H. Masuda, N. Shibata
  • Journal Title: Chem. Comm. Volume: 49 Issue: 95 Pages: 11206-11208
  • DOI: 10.1039/c3cc46544f
  • Peer Reviewed
• [Journal Article] Stereoselective Synthesis of Vinyl Triflones and Heteroaryl Triflones via Anionic O→Cvinyl/N→Cvinyl Trifluoromethanesulfonyl Migration Reacti ons (2013)
  • Author(s): Xiu-Hua Xu, Misaki Taniguchi, Xin Wang, Etsuko Tokunaga, Tomohiro Ozawa, Hideki Masuda, Norio Shibata
  • Journal Title: Angewandte Chemie International Edition Volume: 52巻48号 Issue: 48 Pages: 12628-12631
  • DOI: 10.1002/anie.201307535
  • Peer Reviewed
• [Journal Article] Regioselective 1,4-Trifluoromethylation of α, β-Unsaturated Ketones via a S-(trifluoromethyl)diphenylsulfonium salts/Copper System (2013)
  • Author(s): S. Okusu, Y. Sugita, E. Tokunaga, N, Shibata
  • Journal Title: Beilstein J. Org. Chem. Volume: 9 Pages: 2189-2193
  • DOI: 10.3762/bjoc.9.257
  • Peer Reviewed
• [Journal Article] Organocatalytic Asymmetric Synthesis of Trifluoromethyl-substituted Diarylpyrrolines via Enantioselective Conjugated Cyanation to β-Aryl-β-trifluoromethyl-disubstituted Enones (2012)
  • Author(s): Hiroyuki Kawai
  • Journal Title: Angewandte Chemie International Edition Volume: 51 Issue: 20 Pages: 4959-4962
  • DOI: 10.1002/anie.201201278
  • Peer Reviewed
• [Journal Article] Cation versus Radical: Studies on the C/O Regioselectivity in Electrophilic Tri-, Di- and Monofluoromethylations of β-Ketoesters (2012)
  • Author(s): Y.-D. Yang
  • Journal Title: ChemistryOpen. Volume: 1 Issue: 5 Pages: 221-226
  • DOI: 10.1002/open.201200032
  • Peer Reviewed
• [Journal Article] Efficient Difluoromethylation of sp3 Carbon Nucleophiles by Bromodifluoromethylation Reagents with Organic Bases (2012)
  • Author(s): G.-K. Liu
  • Journal Title: ChemistryOpen. Volume: 1 Issue: 5 Pages: 227-231
  • DOI: 10.1002/open.201200033
  • Peer Reviewed
• [Journal Article] C-F Bond Activation of Unactivated Aliphatic Fluorides: Synthesis of Fluoromethyl-3,5-diaryl-2-oxazolidinones by Desymmetrization of 2-Aryl-1,3-difluoropropan-2-ols (2012)
  • Author(s): G. Haufe
  • Journal Title: Angew. Chem. Int. Ed. Volume: 51 Issue: 49 Pages: 12275-12279
  • DOI: 10.1002/anie.201207304
  • Peer Reviewed
• [Journal Article] 3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocatalyst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes (2012)
  • Author(s): Y.-D. Yang
  • Journal Title: J. Fluorine Chem. Volume: 143 Pages: 204-209
  • DOI: 10.1016/j.jfluchem.2012.06.007
  • Peer Reviewed
• [Journal Article] N-2-Iodobenzylcindhoninium bromide is effective for catalytic enantioselective trifluoromethylation of azomethine imines in Solkane(R) 365mfc (2012)
  • Author(s): Satoshi Okusu
  • Journal Title: Journal of Fluorine Chemistry Volume: 143 Pages: 216-219
  • DOI: 10.1016/j.jfluchem.2012.06.008
  • Peer Reviewed
• [Presentation] Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Trifluoromethylthiolation (2014)
  • Author(s): Norio Shibata
  • Organizer: University of Florida Lecture
  • Place of Presentation: University of Florida (Gainesville，USA)
  • Invited
• [Presentation] Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Trifluoromethylthiolation (2014)
  • Author(s): Norio Shibata
  • Organizer: SynQuest Laboratories. Inc. Lecture
  • Place of Presentation: SynQuest Laboratories. Inc.(Gainesville，USA)
  • Invited
• [Presentation] Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Trifluoromethylthiolation (2014)
  • Author(s): Norio Shibata
  • Organizer: IBM research center Lecture
  • Place of Presentation: IBM research center (San Jose，USA)
  • Invited
• [Presentation] Kinetic Resolution of Allylic Fluorides by Enantioselective Allylic Trifluoromethylation based on Silicon-assisted C-F Bond Cleavage (2014)
  • Author(s): Norio Shibata
  • Organizer: ZING Conference(Asymmetric Synthesis Conference)
  • Place of Presentation: Parador de Nerja (Nerja，Spain)
  • Invited
• [Presentation] Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Trifluoromethylthiolation (2014)
  • Author(s): Norio Shibata
  • Organizer: University of Rouen Lecture
  • Place of Presentation: University of Rouen (Rouen，France)
  • Invited
• [Presentation] フルオロホルムを用いたトリフルオロメチル化 (2014)
  • Author(s): 鈴木悟，大楠賢，徳永恵津子，柴田哲男
  • Organizer: 日本農薬学会第39回大会
  • Place of Presentation: 京都大学（京都）
• [Presentation] 不斉トリフルオロメチル化反応を用いたエイズ治療薬Efavirenzの触媒的合成法開発 (2014)
  • Author(s): 安田吉将，大楠賢，河合洋幸，杉田豊，徳永恵津子，柴田哲男
  • Organizer: 日本農薬学会第39回大会
  • Place of Presentation: 京都大学（京都）
• [Presentation] HFを用いた触媒的不斉フッ素化反応の開発 (2014)
  • Author(s): 加茂智浩，鈴木悟，平松孝章，福士和伸，徳永恵津子，柴田哲男
  • Organizer: 日本農薬学会第39回大会
  • Place of Presentation: 京都大学（京都）
• [Presentation] C-F結合活性化を伴う光学活性含フッ素イソキサゾリン誘導体の合成 (2014)
  • Author(s): 西峯貴之，福士和伸，柴田直幸，平等尋巳，徳永恵津子，柴田哲男
  • Organizer: 日本農薬学会第39回大会
  • Place of Presentation: 京都大学（京都）
• [Presentation] HFをフッ素源としたヨードアレーン触媒によるフッ素化反応 (2014)
  • Author(s): 鈴木悟，加茂智浩，平松孝章，徳永恵津子，柴田哲男
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋大学東山キャンパス（名古屋）
• [Presentation] C-F結合活性化反応によるオキサゾリジノンの合成及び生理活性評価 (2014)
  • Author(s): 田中隼紀，鈴木悟，寺田知里，徳永恵津子，柴田哲男
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋大学東山キャンパス（名古屋）
• [Presentation] 新規光学活性含フッ素超原子価ヨウ素試薬の開発研究 (2014)
  • Author(s): 平等尋巳，西峯貴之，徳永恵津子，柴田哲男
  • Organizer: 日本化学会第94春季年会
  • Place of Presentation: 名古屋大学東山キャンパス（名古屋）
• [Presentation] Trifluoroethoxy-Coated Subphthalocyanines: Synthesis, Characterization, Reactivity and Solubility (2013)
  • Author(s): Norio Shibata
  • Organizer: 245th ACS National Meeting & Exposition
  • Place of Presentation: New Orleans Morial Convention Center(New Orleans, USA)
  • Invited
• [Presentation] First Synthesis of Benzene-fused Hetero-dimers of Phthalocyanine and Subphthalocyanine (2013)
  • Author(s): Norio Shibata
  • Organizer: 4th Japan-Korea-China Joint Seminar on Fluorine Chemistry
  • Place of Presentation: WING AICHI(Nagoya, Japan)
  • Invited
• [Presentation] Kinetic Resolution of Fluorinated Morita-Baylis-Hillman Adducts by Enantioselective Trifluoromethylation (2013)
  • Author(s): Kazunobu Fukushi, Takayuki Nishimine, Naoyuki Shibata, Etsuko Tokunaga, Norio Shibata
  • Organizer: UK/Japan Conference in Catalytic Asymmetric Synthesis
  • Place of Presentation: 仙台国際センター（仙台）
• [Presentation] 医農薬合成を指向した含フッ素複素環化合物の合成(依頼セミナー） (2013)
  • Author(s): 柴田哲男
  • Organizer: CPhI Japan 2013国際医薬品原料/中間体展
  • Place of Presentation: 東京ビッグサイト 東4・5ホール（東京）
  • Invited
• [Presentation] β，β‐二置換トリフルオロメチルエノンへのメチルヒドラジンによる酸素分子を酸化剤に用いた不斉エポキシ化反応の開発 (2013)
  • Author(s): 大楠賢，河合洋幸，徳永恵津子，柴田哲男
  • Organizer: 第20回記念シンポジウム「モレキュラー・キラリティー2013」
  • Place of Presentation: 京都大学（京都）
• [Presentation] 速度論的光学分割による光学活性フッ素化 Morita-Baylis-Hillman 誘導体の合成法開発 (2013)
  • Author(s): 福士和伸，西峯貴之，柴田直幸，徳永恵津子，柴田哲男
  • Organizer: 第20回記念シンポジウム「モレキュラー・キラリティー2013」
  • Place of Presentation: 京都大学（京都）
• [Presentation] Enantioselective Synthesis of Biologically Active Molecules having a CF3 Quaternary Carbon (2013)
  • Author(s): Norio Shibata
  • Organizer: Shanghai Institute of Organic Chemistry Lecture
  • Place of Presentation: Shanghai Institute of Organic Chemistry(Shinghai, China)
  • Invited
• [Presentation] Enantioselective Synthesis of Biologically Active Molecules having a CF3 Quaternary Carbon (2013)
  • Author(s): Norio Shibata
  • Organizer: East China Nomal University Lecture
  • Place of Presentation: East China Nomal University(Shinghai, China)
  • Invited
• [Presentation] Enantioselective Synthesis of Biologically Active Molecules having a CF3 Quaternary Carbon (2013)
  • Author(s): Norio Shibata
  • Organizer: East China University of Science And Technology Lecture
  • Place of Presentation: East China University of Science And Technology(Shinghai, China)
  • Invited
• [Presentation] Enantioselective Synthesis of Biologically Active Molecules having a CF3 Quaternary Carbon (2013)
  • Author(s): Norio Shibata
  • Organizer: Lanzhou Institute of Chemical Physics Lecture
  • Place of Presentation: Lanzhou Institute of Chemical Physics (LICP)(Lanzhou, China)
  • Invited
• [Presentation] Enantioselective Synthesis of Biologically Active Molecules having a CF3 Quaternary Carbon Triuoroethoxy-Coated Subphthalocyanines:Synthesis, Characterization, Reactivity and Solubility (2013)
  • Author(s): Norio Shibata
  • Organizer: Northwest Normal University Lecture
  • Place of Presentation: Northwest Normal University (Lanzhou ,China)
  • Invited
• [Presentation] Enantioselective Synthesis of Biologically Active Molecules having a CF3 Quaternary Carbon (2013)
  • Author(s): Norio Shibata
  • Organizer: Lanzhou University Lecture
  • Place of Presentation: Lanzhou University (Lanzhou, China)
  • Invited
• [Presentation] Enantioselective Synthesis of Biologically Active Molecules having a CF3 Quaternary Carbon (2013)
  • Author(s): Norio Shibata
  • Organizer: Zhejiang University of Industry Lecture
  • Place of Presentation: Zhejiang University of Industry(Zhejiang, China)
  • Invited
• [Presentation] Enantioselective Synthesis of Biologically Active Molecules having a CF3 Quaternary Carbon (2013)
  • Author(s): Norio Shibata
  • Organizer: Zhejiang University Lecture
  • Place of Presentation: Zhejiang University (Zhejiang ，China)
  • Invited
• [Presentation] Enantioselective Synthesis of Epoxides having a Tetrasubstituted Trifluoromethylated Carbon Center by Methylhydrazine-induced Non-metallic Aerobic Epoxidation of β,β-Disubstituted Enones (2013)
  • Author(s): Satoshi Okusu, Hiroyuki Kawai, Zhe Yuan, Etsuko Tokunaga, Norio Shibata
  • Organizer: Nagoya Symposium 2013
  • Place of Presentation: 名古屋大学（名古屋）
• [Presentation] 選択的C-F 結合活性化反応を用いるモノフルオロメチルオキサゾリジノン類の合成 (2013)
  • Author(s): 鈴木悟，寺田知里，徳永恵津子，柴田哲男
  • Organizer: 第11 回次世代を担う有機化学シンポジウム
  • Place of Presentation: 日本薬学会長井記念ホール（東京）
• [Presentation] Enantioselective Synthesis of Epoxides having a Tetrasubstituted Trifluoromethylated Carbon Center by Methylhydrazine-induced Non-metallic Aerobic Epoxidation of β,β-Disubstituted Enones (2013)
  • Author(s): Norio Shibata
  • Organizer: 1st International Conference & 6th Symposium of Organocatalysis
  • Place of Presentation: Prince Hotel Otsu（Otsu, Japan)
  • Invited
• [Presentation] Enantioselective Synthesis of Epoxide by methylhydrazine-induced Aerobic Epoxidation of β-trifluoromethyl-β,β-disubstituted enones (2013)
  • Author(s): Satoshi Okusu, Hiroyuki Kawai, Zhe Yuan, Etsuko Tokunaga, Norio Shibata
  • Organizer: 6th Symposium of Organocatalysis
  • Place of Presentation: Prince Hotel Otsu（Otsu, Japan)
• [Presentation] 3,5-Bis(pentafluorosulfanyl)phenylboronic acid: A new organocataryst for Conia-ene carbocyclization of 1,3-dicarbonyl compounds having terminal alkynes (2013)
  • Author(s): Yu-Dong Yang, Xu Lu, Etsuko Tokunaga, Norio Shibata
  • Organizer: 6th Symposium of Organocatalysis
  • Place of Presentation: Prince Hotel Otsu（Otsu, Japan)
• [Presentation] Enantioselective Monofluoromethylation of Indol Derivatives Using FBSM (2013)
  • Author(s): Kohei Matsuzaki, Tatsuya Furukawa, Etsuko Tokunaga, Norio Shibata
  • Organizer: 6th Symposium of Organocatalysis
  • Place of Presentation: Prince Hotel Otsu（Otsu, Japan)
• [Presentation] Copper-Catalyzed Triuoromethylthiolation of Indol and β-Keto Esters (2013)
  • Author(s): 東綾香，楊宇東，徳永恵津子，山崎幹男，城始勇，柴田哲男
  • Organizer: 第５９回日本薬学会東海支部 総会・大会
  • Place of Presentation: 名城大学薬学部（名古屋）
• [Presentation] Selective O-difluoromethylation of 1,3-Dinones by Bromodifluoromethylating reagents (2013)
  • Author(s): 王欣，劉国凱，徐修華，徳永恵津子，柴田哲男
  • Organizer: 第５９回日本薬学会東海支部 総会・大会
  • Place of Presentation: 名城大学薬学部（名古屋）
• [Presentation] 超原子価ヨウ素を用いた触媒的フッ素化反応の開発 (2013)
  • Author(s): 加茂智浩，鈴木悟，福士和伸，徳永恵津子，柴田哲男
  • Organizer: 第５９回日本薬学会東海支部 総会・大会
  • Place of Presentation: 名城大学薬学部（名古屋）
• [Presentation] 超原子価ヨウ素試薬を用いた非対称ビアリール化合物の酸化的トリフルオロメチル化反応の開発研究 (2013)
  • Author(s): 岩本寛治，楊宇東，徳永恵津子，柴田哲男
  • Organizer: 第５９回日本薬学会東海支部 総会・大会
  • Place of Presentation: 名城大学薬学部（名古屋）
• [Presentation] Trifluoromethylsulfonyl Hypervalent Iodonium Yilede for Copper-Catalyzed Trifluoromethylthiolation of Enamines (2013)
  • Author(s): 楊宇東，東綾香，徳永恵津子，柴田哲男
  • Organizer: 第５９回日本薬学会東海支部 総会・大会
  • Place of Presentation: 名城大学薬学部（名古屋）
• [Presentation] 超原子価ヨウ素を用いた触媒的フッ素化反応の開発 (2013)
  • Author(s): 福士和伸，加茂智浩，鈴木 悟，徳永恵津子，柴田哲男
  • Organizer: 日本プロセス化学会2013 サマーシンポジウム
  • Place of Presentation: つくば国際会議場（筑波）
• [Presentation] FBSM を用いるモノフルオロメチルインドール類のOne-Pot 型不斉合成 (2013)
  • Author(s): 松崎浩平，古川達也，徳永恵津子，柴田哲男
  • Organizer: 日本プロセス化学会2013 サマーシンポジウム
  • Place of Presentation: つくば国際会議場（筑波）
• [Presentation] 超原子価ヨウ素試薬を用いた非対称ビアリール化合物のトリフルオロメチル化反応の開発研究 (2013)
  • Author(s): 岩本寛治，楊宇東，徳永恵津子，柴田哲男
  • Organizer: 日本プロセス化学会2013 サマーシンポジウム
  • Place of Presentation: つくば国際会議場（筑波）
• [Presentation] 複核型含フッ素サブフタロシアニンの合成 (2013)
  • Author(s): 大井翔太，森悟，徳永恵津子，柴田哲男
  • Organizer: 日本プロセス化学会2013 サマーシンポジウム
  • Place of Presentation: つくば国際会議場（筑波）
• [Presentation] Enantioselective Synthesis of Epoxides Having a Tetrasubstituted Trifluoromethylated Carbon Center: Methylhydrazine-Induced Aerobic Epoxidation of β,β,-Disubstituted Enones (2013)
  • Author(s): Norio Shibata
  • Organizer: 17th European Symposium on Fluorine Chemistry(17ESFC)
  • Place of Presentation: Paris Descartes University (Paris, France)
• [Presentation] 酸化剤を用いる触媒的フッ素化反応の開発 (2013)
  • Author(s): 加茂智浩，鈴木悟，福士和伸，徳永恵津子，柴田哲男
  • Organizer: 第３回フッ素化学 若手の会
  • Place of Presentation: 琵琶湖リゾートクラブ（守山）
• [Presentation] Thia-Fries 転位を用いたビニルトリフロンの合成 (2013)
  • Author(s): 谷口海紗生，徐修華，徳永恵津子，柴田哲男
  • Organizer: 第３回フッ素化学 若手の会
  • Place of Presentation: 琵琶湖リゾートクラブ（守山）
• [Presentation] Enantioselective Monofluoromethylation of Indole Derivatives Using FBSM (2013)
  • Author(s): Kohei Matsuzaki, Tatsuya Furukawa, Etsuko Tokunaga, Norio Shibata
  • Organizer: The 15th Asian Chemical Congress
  • Place of Presentation: Resorts World Sentosa (Singapore)
• [Presentation] Enantioselective Synthesis of Epoxides by Methylhydrazine-induced Aerobic Epoxidation of Trifluoromethyl-substituted Enones (2013)
  • Author(s): Satoshi Okusu, Hiroyuki Kawai, Zhe Yuan, Etsuko Tokunaga, Norio Shibata
  • Organizer: The 15th Asian Chemical Congress
  • Place of Presentation: Resorts World Sentosa (Singapore)
• [Presentation] Organocatalyzed Asymmetric Allylic Trifluoromethylation and Kinetic Resolution Using Ruppert’s Reagent (2013)
  • Author(s): Takayuki Nishimine, Kazunobu Fukishi, Naoyuki Shibata, Etsuko Tokunaga, Norio Shibata
  • Organizer: The 15th Asian Chemical Congress
  • Place of Presentation: Resorts World Sentosa (Singapore)
• [Presentation] Enantioselective Synthesis of Organouorine Compounds (2013)
  • Author(s): Norio Shibata
  • Organizer: International Workshop on Organouorine Chemistry 2013
  • Place of Presentation: Nanjing University of Science & Technology(Nanjing, Chaina)
  • Invited
• [Presentation] Enantioselective Synthesis of Organouorine Compounds (2013)
  • Author(s): Norio Shibata
  • Organizer: Changzhou University Lecture
  • Place of Presentation: Changzhou University(Changzhou, Chaina)
  • Invited
• [Presentation] A Sterically Demanding Organo-superbase Avoids Decomposition of a Naked Trifluoromethyl Carbanion Directly Generated from Fluoroform (2013)
  • Author(s): Norio Shibata
  • Organizer: 10th International Symposium on Carbanion Chemistry (ISCC-10)
  • Place of Presentation: Doshisha University(Kyoto, Japan)
  • Invited
• [Presentation] Palladium Catalyzed Allylation of α-trifluoromethyl carbanions (2013)
  • Author(s): Kazunobu Fukushi, Tatsuya Furukawa, Satoru suzuki, Etsuko Tokunaga, Norio Shibata
  • Organizer: 10th International Symposium on Carbanion Chemistry (ISCC-10)
  • Place of Presentation: Doshisha University(Kyoto, Japan)
• [Presentation] Organocatalytic Enantioselective Monofluoromethylation of Indoles Using FBSM (2013)
  • Author(s): Kohei Matsuzaki, Tatsuya Furukawa, Etsuko Tokunaga, Norio Shibata
  • Organizer: 10th International Symposium on Carbanion Chemistry (ISCC-10)
  • Place of Presentation: Doshisha University(Kyoto, Japan)
• [Presentation] 速度論的光学分割を伴う有機触媒的アリル位不斉フルオロアルキル化反応の開発 (2013)
  • Author(s): 西峯貴之，福士和伸，柴田直幸，平等尋巳，徳永恵津子，柴田哲男
  • Organizer: 第36回フッ素化学討論会
  • Place of Presentation: エポカルつくば（茨城）
• [Presentation] 選択的炭素-フッ素結合活性化反応を経由する含フッ素有機化合物の合成 (2013)
  • Author(s): 田中隼紀，鈴木 悟，寺田知里，徳永恵津子，柴田哲男
  • Organizer: 第36回フッ素化学討論会
  • Place of Presentation: エポカルつくば（茨城）
• [Presentation] Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Trifluoromethylthiolation (2013)
  • Author(s): Norio Shibata
  • Organizer: 9th AFMC International Medicinal Chemistry Symposium(AIMECS13)
  • Place of Presentation: The Grand Hotel (Taipei, Taiwan)
  • Invited
• [Presentation] A new reagent for electrophilic trifluoromethylthiolation (2013)
  • Author(s): Norio Shibata
  • Organizer: 14th Tetrahedron Symposium Asian Edition
  • Place of Presentation: Ritz Carlton Seoul (Seoul, Korea)
  • Invited
• [Presentation] 超原子価ヨウ素イリドを用いる新規トリフルオロメチルチオ化反応の開発 (2013)
  • Author(s): 東綾香，楊宇東，徳永恵津子，柴田哲男
  • Organizer: 第3回CSJ化学フェスタ2013
  • Place of Presentation: タワーホール船堀（東京）
• [Presentation] 触媒的フッ素化反応の開発 (2013)
  • Author(s): 加茂智浩，鈴木悟，福士和伸，平松孝章，徳永恵津子，柴田哲男
  • Organizer: 第3回CSJ化学フェスタ2013
  • Place of Presentation: タワーホール船堀（東京）
• [Presentation] 速度論的光学分割を伴う有機触媒的不斉フルオロアルキル化反応の開発 (2013)
  • Author(s): 平等尋巳，西峯貴之，福士和伸，柴田直幸，徳永恵津子，柴田哲男
  • Organizer: 第3回CSJ化学フェスタ2013
  • Place of Presentation: タワーホール船堀（東京）
• [Presentation] 炭素-フッ素（C-F）結合活性化反応を用いたモノフルオロメチルオキサゾリジノンの合成研究 (2013)
  • Author(s): 寺田知里，鈴木悟，田中隼紀，徳永恵津子，柴田哲男
  • Organizer: 第3回CSJ化学フェスタ2013
  • Place of Presentation: タワーホール船堀（東京）
• [Presentation] トリフルオロメチル基を有するフタロシアニンの簡便な合成法の開発 (2013)
  • Author(s): 飯田紀士，田中健太，徳永恵津子，柴田哲男
  • Organizer: 第44回 中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 静岡大学（浜松）
• [Presentation] S-(Phenylsulfonyldifluoromethyl)thiopheniumsalts: A new and highly efficient difluoromethylation reagents for sp3-C nucleophilies (2013)
  • Author(s): 王 欣，劉国凱，徐修華，徳永恵津子，柴田哲男
  • Organizer: 第44回 中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 静岡大学（浜松）
• [Presentation] Trifluoromethanesulfonyl Hypervalent Iodonium Ylide: A Novel Reagent for Trifluoromethylthiolation (2013)
  • Author(s): 楊宇東，東綾香，徳永恵津子，山崎幹男，城始勇，柴田哲男
  • Organizer: 第44回 中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 静岡大学（浜松）
• [Presentation] 不斉フルオロアルキル化反応による含フッ素森田－ベイリス－ヒルマン付加体の速度論的光学分割 (2013)
  • Author(s): 西峯貴之，福士和伸，柴田直幸，平等尋巳，徳永恵津子，柴田哲男
  • Organizer: 第44回 中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 静岡大学（浜松）
• [Presentation] 新規キラル超原子価ヨウ素試薬の開発とそれを用いた不斉反応への展開 (2013)
  • Author(s): 平等尋巳，西峯貴之，徳永恵津子，柴田哲男
  • Organizer: 第44回 中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 静岡大学（浜松）
• [Presentation] 超原子価ヨウ素を介した触媒的フッ素化反応 (2013)
  • Author(s): 平松孝章，鈴木悟，加茂智浩，福士和伸，徳永恵津子，柴田哲男
  • Organizer: 第44回 中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 静岡大学（浜松）
• [Presentation] 求核的フッ素化剤を用いた超原子価ヨウ素試薬による触媒的フッ素化反応 (2013)
  • Author(s): 鈴木悟，加茂智浩，徳永恵津子，柴田哲男
  • Organizer: 第39回反応と合成の進歩シンポジウム
  • Place of Presentation: 九州大学（福岡）
• [Presentation] フルオロホルムを用いたトリフルオロメチル化反応 (2013)
  • Author(s): 柴田哲男
  • Organizer: フッ素化学第１５５委員会第95回研究会
  • Place of Presentation: 兵庫県民会館けんみんホール（神戸）
  • Invited
• [Presentation] 超原子価ヨウ素イリド骨格を有する新規トリフルオロメチルチオ化反応の開発 (2013)
  • Author(s): 東綾香，楊宇東，徳永恵津子，柴田哲男
  • Organizer: 第28回農薬デザイン研究会
  • Place of Presentation: メルパルク京都（京都）
• [Presentation] フルオロホルムを用いたトリフルオロメチル化反応の開発 (2013)
  • Author(s): 大楠 賢，河合洋幸，杉田 豊，徳永恵津子，柴田哲男
  • Organizer: 第28回農薬デザイン研究会
  • Place of Presentation: メルパルク京都（京都）
• [Presentation] S-(Phenylsulfonyldifluoromethyl)thiopheniumsalts: A New and Highly Efficient Difluoromethylation Reagents for sp3-C Nucleophilies (2013)
  • Author(s): 王欣，劉国凱，徐修華，徳永恵津子，柴田哲男
  • Organizer: 第28回農薬デザイン研究会
  • Place of Presentation: メルパルク京都（京都）
• [Presentation] 不斉トリフルオロメチル化反応による速度論敵光学分割を鍵反応とした光学活性含フッ素イソキサゾリン誘導体の合成 (2013)
  • Author(s): 西峯貴之，福士和伸，柴田直幸，平等尋巳，徳永恵津子，柴田哲男
  • Organizer: 第28回農薬デザイン研究会
  • Place of Presentation: メルパルク京都（京都）
• [Presentation] HFを用いた有機化合物への触媒的フッ素化反応 (2013)
  • Author(s): 鈴木悟，加茂智浩，平松孝章，徳永恵津子，柴田哲男
  • Organizer: 第28回農薬デザイン研究会
  • Place of Presentation: メルパルク京都（京都）
• [Presentation] ヨウ素触媒を用いたフッ素化反応 (2013)
  • Author(s): 鈴木悟，加茂智浩，平松孝章，徳永恵津子，柴田哲男
  • Organizer: 第40回 有機典型元素化学討論会
  • Place of Presentation: 近畿大学（大阪）
• [Presentation] Trifluoromethanesulfonyl Hypervalent Iodonium Ylide for Trifluoromethylthiolation (2013)
  • Author(s): Norio Shibata
  • Organizer: Changwon National University Lecture
  • Place of Presentation: Changwon National University (Changwon, Korea)
  • Invited
• [Presentation] Enantiocontrolled Synthesis of Organofluorine Compounds, BIT’s 3nd Annual World Congress of Catalytic Asymmetric Synthesis (2012)
  • Author(s): 柴田哲男
  • Organizer: WCCAS-2012
  • Place of Presentation: Beijing, China
  • Invited
• [Presentation] Recent Progress of Fluoromethylation Reactions, 3rd International Symposium on Organofluorine Compounds in Biomedical, Materials and Agricultural Sciences (2012)
  • Author(s): 柴田哲男
  • Organizer: Valencia Fluorine Days
  • Place of Presentation: Valencia, Spain
  • Invited
• [Presentation] トリフルオロメチル化試薬の開発 (2012)
  • Author(s): 柴田哲男
  • Organizer: 文部科学省科学研究費補助金 「有機分子触媒による未来型分子変換」 第1回全体会議
  • Place of Presentation: 京都
  • Invited
• [Presentation] Development of Shelf-stable Electrophilic Trifluoromethylating Reagents (2012)
  • Author(s): 柴田哲男
  • Organizer: 8th Japanese-French Joint Seminar on Fluorine Chemistry
  • Place of Presentation: 京都
  • Invited
• [Presentation] ENANTIOSELECTIVE SYNTHESIS OF FLUORO-ORGANIC COMPOUNDS (2012)
  • Author(s): 柴田哲男
  • Organizer: 20th International Symposium on Fluorine Chemistry
  • Place of Presentation: 京都
  • Invited
• [Presentation] Trifluoroethoxy-Coated Subphthalocyanines:Synthesis, Characterization, Reactivity and Solubility (2012)
  • Author(s): 柴田哲男
  • Organizer: 17th Malaysian Chemical Congress (17MCC)
  • Place of Presentation: Kuala Lumpur, Malaysia
  • Invited
• [Presentation] Enantioselective 5-Endo-dig Carbocyclization with Internal Alkynes using a Combinatorial Box-Ph/Zn(II)/Yb(OTf)3/HFIP System (2012)
  • Author(s): 柴田哲男
  • Organizer: Cambodian Malaysian Chemical Conference (CMCC)
  • Place of Presentation: Siem Reap, Cambodia
  • Invited
• [Presentation] サブフタロシアニン色素（フッ素と化学工業） (2012)
  • Author(s): 柴田哲男
  • Organizer: 東海化学工業会セミナー
  • Place of Presentation: 名古屋
  • Invited
• [Presentation] フッ素が創る新しいサブフタロシアニンとそのπ空間 (2012)
  • Author(s): 柴田哲男
  • Organizer: 第43回 中部化学関係学協会支部連合秋季大会
  • Place of Presentation: 名古屋
  • Invited
• [Presentation] Enantioselective Synthesis of Partially Saturated Fluorinated Heterocycles, Fluorine Chemistry to Environment and Health Aspects (2012)
  • Author(s): 柴田哲男
  • Organizer: Dasan Conference
  • Place of Presentation: Changwon, South Korea
  • Invited
• [Presentation] Enantioselective Synthesis of Partially Saturated Fluorinated Heterocycles (2012)
  • Author(s): 柴田哲男
  • Organizer: First Japan-USA Organocatalytic Symposium
  • Place of Presentation: Honolulu, lHawaii, USA
  • Invited