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9 article(s) from Shibata, Norio

Synthesis of trifluoromethyl ketones by nucleophilic trifluoromethylation of esters under a fluoroform/KHMDS/triglyme system

Yamato Fujihira,
Yumeng Liang,
Makoto Ono,
Kazuki Hirano,
Takumi Kagawa and
Norio Shibata

Letter
Published 12 Feb 2021

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1. Graphical Abstract
2. Scheme 1: Chemistry of the CF₃ anion generated from HCF₃. a) Decomposition of the trifluoromethyl anion to di...
  
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3. Figure 1: Trifluoromethyl ketones. a) Hydrolysis of trifluoromethyl ketones. b) Selected examples of biologic...
  
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4. Scheme 2: Trifluoromethylation of esters by HCF₃ by a) Russell and Roques (1998), b) Prakash and co-workers (...
  
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5. Scheme 3: Substrate scope of esters 1 for trifluoromethylation by HCF₃ under the optimized conditions. ^aDeter...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2021, 17, 431–438, doi:10.3762/bjoc.17.39

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Deoxyfluorination of acyl fluorides to trifluoromethyl compounds by FLUOLEAD^®/Olah’s reagent under solvent-free conditions

Yumeng Liang,
Akihito Taya,
Zhengyu Zhao,
Norimichi Saito and
Norio Shibata

Letter
Published 14 Dec 2020

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1. Graphical Abstract
2. Figure 1: Ratios of CF₃-containing drugs in marketed fluoro-pharmaceuticals and registered fluoro-agrochemica...
  
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3. Figure 2: Selected examples of CF₃-containing biologically active molecules.
  
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4. Scheme 1: Transformation of acyl fluorides to trifluoromethyl compounds. a) Deoxyfluorination of acyl fluorid...
  
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5. Scheme 2: The substrate scope of acyl fluorides. Reaction conditions: 1 (0.3 mmol), FLUOLEAD^® (0.9 mmol, 3.0 ...
  
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6. Scheme 3: Mechanism of deoxyfluorination of acyl fluorides 1 with FLUOLEAD^®/Olah’s reagent to trifluoromethyl...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2020, 16, 3052–3058, doi:10.3762/bjoc.16.254

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Synthesis of fluoro-functionalized diaryl-λ³-iodonium salts and their cytotoxicity against human lymphoma U937 cells

Prajwalita Das,
Etsuko Tokunaga,
Hidehiko Akiyama,
Hiroki Doi,
Norimichi Saito and
Norio Shibata

Full Research Paper
Published 07 Feb 2018

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1. Graphical Abstract
2. Figure 1: Compounds used for the biological study.
  
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3. Figure 2: Compounds 1–4 induced cell death in U937 cells. Briefly, U937 cells (1 × 10⁴ cells/mL) were incubat...
  
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4. Scheme 1: Synthesis of pentafluoro-(2-iodophenyl)-λ⁶-sulfane (7).
  
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5. Scheme 2: Synthesis of unsymmetrical ortho-SF₅ diaryliodonium salts 3p, 4b, 5a and 6a.
  
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6. Figure 3: X-ray crystallographic structure of 3p drawn at 50% probability (CCDC 1573953).
  
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7. Figure 4: Ortho-SF₅ phenyl iodonium salts 3p and 5a and their structural components 7 and 9 induced cell deat...
  
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8. Figure 5: 3k, 3m and 3p induced cell death in AGLCL, a human normal B cell line. Briefly, AGLCL cells (1 × 10⁴...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2018, 14, 364–372, doi:10.3762/bjoc.14.24

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Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides

Masanori Inaba,
Tatsuya Sakai,
Shun Shinada,
Tsuyuka Sugiishi,
Yuta Nishina,
Norio Shibata and
Hideki Amii

Full Research Paper
Published 19 Jan 2018

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1. Graphical Abstract
2. Scheme 1: Phthalide and fluorinated phthalides (1).
  
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3. Scheme 2: Plausible reaction mechanism for the formation of phthalide 1a.
  
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4. Scheme 3: Synthesis of fluorinated phthalides 1.
  
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5. Scheme 4: Asymmetric synthesis of 1a using a chiral auxiliary.
  
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6. Scheme 5: Catalytic asymmetric synthesis of 1a.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2018, 14, 182–186, doi:10.3762/bjoc.14.12

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Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

Satoru Mori and
Norio Shibata

Review
Published 27 Oct 2017

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1. Graphical Abstract
2. Scheme 1: Synthesis of trifluoroethoxy-substituted phthalocyanine.
  
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3. Scheme 2: Synthesis of trifluoroethoxy-substituted binuclear phthalocyanine 5 in Solkane^® 365 mfc.
  
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4. Scheme 3: Synthesis of trifluoroethoxy-substituted unsymmetrical phthalocyanines.
  
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5. Scheme 4: Synthesis of trifluoroethoxy-substituted phthalocyanine dimers linked at the β-position.
  
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6. Figure 1: Structure of trifluoroethoxy-substituted phthalocyanine dimers linked at the α-position.
  
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7. Figure 2: Structure of trifluoroethoxy-substituted dimer via a diacetylene linker.
  
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8. Figure 3: UV–vis spectra of 9 (A) and 5 (B).
  
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9. Figure 4: Structure of binuclear phthalocyanines linked by a triazole linker.
  
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10. Figure 5: Structure of trinuclear phthalocyanines linked by a triazole linker, and windmill-like molecular st...
  
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11. Scheme 5: Synthesis of trifluoroethoxy-substituted phthalocyanines conjugated with peptides.
  
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12. Scheme 6: Synthesis of trifluoroethoxy-substituted phthalocyanines conjugated with deoxyribonucleosides.
  
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13. Scheme 7: Synthesis of trifluoroethoxy-substituted phthalocyanines conjugated with cyclodextrin.
  
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14. Figure 6: Direction of energy transfer of phthalocyanine–fullerene conjugates.
  
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15. Scheme 8: Synthesis of fluoropolymer-bearing phthalocyanine side groups.
  
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16. Scheme 9: Synthesis of trifluoroethoxy-substituted double-decker type phthalocyanines.
  
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17. Scheme 10: Synthesis of trifluoroethoxy-substituted subphthalocyanine.
  
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18. Figure 7: Structure of axial ligand substituted subphthalocyanine hybrid dyes.
  
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19. Scheme 11: Synthesis of subphthalocyanine homodimers.
  
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20. Scheme 12: Synthesis of subphthalocyanine heterodimers.
  
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21. Figure 8: Energy transfer between subphthalocyanine units.
  
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22. Figure 9: Structure of phthalocyanine and subphthalocyanine benzene-fused homodimers.
  
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23. Scheme 13: Synthesis of a phthalocyanine and subphthalocyanine benzene-fused heterodimer.
  
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24. Figure 10: X-ray crystallography of Pc-subPc (left) and UV–vis spectra of benzene-fused dimers.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

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Regioselective 1,4-trifluoromethylation of α,β-unsaturated ketones via a S-(trifluoromethyl)diphenylsulfonium salts/copper system

Satoshi Okusu,
Yutaka Sugita,
Etsuko Tokunaga and
Norio Shibata

Letter
Published 23 Oct 2013

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1. Graphical Abstract
2. Scheme 1: Trifluoromethylation of α,β-unsaturated ketones.
  
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3. Scheme 2: Proposed mechanism for the conjugate trifluoromethylation of α,β-unsaturated ketones by S-(trifluor...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2013, 9, 2189–2193, doi:10.3762/bjoc.9.257

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Shelf-stable electrophilic trifluoromethylating reagents: A brief historical perspective

Norio Shibata,
Andrej Matsnev and
Dominique Cahard

Review
Published 16 Jun 2010

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1. Graphical Abstract
2. Scheme 1: Preparation of the first electrophilic trifluoromethylating reagent and its reaction with a thiophe...
  
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3. Scheme 2: Synthetic routes to S-CF₃ and Se-CF₃ dibenzochalcogenium salts.
  
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4. Scheme 3: Synthesis of (trifluoromethyl)dibenzotellurophenium salts.
  
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5. Scheme 4: Nitration of (trifluoromethyl)dibenzochalcogenium salts.
  
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6. Scheme 5: Synthesis of a sulphonium salt with a bridged oxygen.
  
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7. Scheme 6: Reactivity of (trifluoromethyl)dibenzochalcogenium salts.
  
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8. Scheme 7: Pd(II)-Catalyzed ortho-trifluoromethylation of heterocycle-substituted arenes by Umemoto’s reagents....
  
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9. Scheme 8: Mild electrophilic trifluoromethylation of β-ketoesters and silyl enol ethers.
  
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10. Scheme 9: Enantioselective electrophilic trifluoromethylation of β-ketoesters.
  
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11. Scheme 10: Preparation of water-soluble S-(trifluoromethyl)dibenzothiophenium salts.
  
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12. Scheme 11: Method for large-scale preparation of S-(trifluoromethyl)dibenzothiophenium salts.
  
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13. Scheme 12: Triflic acid catalyzed synthesis of 5-(trifluoromethyl)thiophenium salts.
  
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14. Scheme 13: Trifluoromethylation of β-ketoesters and dicyanoalkylidenes by S-(trifluoromethyl)benzothiophenium ...
  
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15. Scheme 14: Synthesis of chiral S-(trifluoromethyl)benzothiophenium salt 18 and attempt of enantioselective tri...
  
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16. Scheme 15: Synthesis of O-(trifluoromethyl)dibenzofuranium salts.
  
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17. Scheme 16: Photochemical O- and N-trifluoromethylation by 20b.
  
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18. Scheme 17: Thermal O-trifluoromethylation of phenol by diazonium salt 19a. Effect of the counteranion.
  
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19. Scheme 18: Thermal O- and N-trifluoromethylations.
  
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20. Scheme 19: Method of preparation of S-(trifluoromethyl)diphenylsulfonium triflates.
  
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21. Scheme 20: Reactivity of some S-(trifluoromethyl)diarylsulfonium triflates.
  
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22. Scheme 21: One-pot synthesis of S-(trifluoromethyl)diarylsulfonium triflates.
  
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23. Scheme 22: One-pot synthesis of Umemoto’s type reagents.
  
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24. Scheme 23: Preparation of sulfonium salts by transformation of CF₃⁻ into CF₃⁺.
  
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25. Scheme 24: Selected reactions with the new Yagupolskii reagents.
  
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26. Scheme 25: Synthesis of heteroaryl-substituted sulfonium salts.
  
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27. Scheme 26: First neutral S-CF₃ reagents.
  
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28. Scheme 27: Synthesis of Togni reagents. ^aYield for the two-step procedure.
  
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29. Scheme 28: Trifluoromethylation of C-nucleophiles with 37.
  
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30. Scheme 29: Selected examples of trifluoromethylation of S-nucleophiles with 37.
  
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31. Scheme 30: Selected examples of trifluoromethylation of P-nucleophiles with 35 and 37.
  
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32. Scheme 31: Trifluoromethylation of 2,4,6-trimethylphenol with 35.
  
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33. Scheme 32: Examples of O-trifluoromethylation of alcohols with 35 in the presence of 1 equiv of Zn(NTf₂)₂.
  
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34. Scheme 33: Formation of trifluoromethyl sulfonates from sulfonic acids and 35.
  
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35. Scheme 34: Organocatalytic α-trifluoromethylation of aldehydes with 37.
  
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36. Scheme 35: Synthesis of reagent 42 and mechanism of trifluoromethylation.
  
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37. Scheme 36: Trifluoromethylation of β-ketoesters and dicyanoalkylidenes with 42.
  
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Graphical Abstract

Beilstein J. Org. Chem. 2010, 6, No. 65, doi:10.3762/bjoc.6.65

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New diarylmethanofullerene derivatives and their properties for organic thin- film solar cells

Daisuke Sukeguchi,
Surya Prakash Singh,
Mamidi Ramesh Reddy,
Hideyuki Yoshiyama,
Rakesh A. Afre,
Yasuhiko Hayashi,
Hiroki Inukai,
Tetsuo Soga,
Shuichi Nakamura,
Norio Shibata and
Takeshi Toru

Full Research Paper
Published 24 Feb 2009

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1. Graphical Abstract
2. Figure 1: Diarylmethanofullerene derivatives.
  
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3. Scheme 1: Synthesis of diarylmethanofullerene derivatives.
  
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4. Figure 2: Device layout of the solar cell.
  
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5. Figure 3: (A) J–V characteristics of the P3HT:1a-blended device annealed at 100–140 °C (black: 100 °C, red: 1...
  
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6. Figure 4: (A) Spectral responsivity of the P3HT:1a-blended film on the ITO glass annealed at 100–140 °C (100 ...
  
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7. Figure 5: The AFM images of the P3HT:1a- and P3HT:PCBM-blended films annealed at different temperatures. (A) ...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2009, 5, No. 7, doi:10.3762/bjoc.5.7

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DBFOX- Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones

Takehisa Ishimaru,
Norio Shibata,
Dhande Sudhakar Reddy,
Takao Horikawa,
Shuichi Nakamura and
Takeshi Toru

Preliminary Communication
Published 20 May 2008

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1. Graphical Abstract
2. Figure 1: Structures of DBFOX-Ph, Box-Ph and NFSI.
  
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3. Scheme 1: Transition-State Structure for the DBFOX-Ph/Ni(II) Catalyzed Enantioselective Fluorination of 1 to 2...
  
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Graphical Abstract

Beilstein J. Org. Chem. 2008, 4, No. 16, doi:10.3762/bjoc.4.16

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