Chinese Journal of Chemistry

Cover image for Vol. 31 Issue 7

Special Issue: Organofluorine Chemistry

July, 2013

Volume 31, Issue 7

Pages 865–954

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
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      Cover Picture: Palladium-Catalyzed Cross-Coupling of Fluorinated Vinyl Chlorides with Terminal Alkynes: A General Protocol to Fluorinated Enynes (Chin. J. Chem. 7/2013) (page 865)

      Sheng Chen, Chunfa Xu, Long Lu and Qilong Shen

      Version of Record online: 22 JUL 2013 | DOI: 10.1002/cjoc.201390016

      Thumbnail image of graphical abstract

      The cover picture shows an efficient and cost-effective method for the preparation of fluorinated conjugated enynes. The method was compatible with a variety of functional groups such as chloride, amine, cyano and ester group. The method could also be extended to the coupling of (R,Z)-3-(2-chloro-1,2-difluorovinyl)-4-alkyloxazolidin-2-one (3) with moderate yields. More details are discussed in the article by Shen et al. on page 901–907.

  2. Editorial

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    3. Editorial
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      Special Issue of "Organofluorine Chemistry" (page 867)

      Jinbo Hu

      Version of Record online: 22 JUL 2013 | DOI: 10.1002/cjoc.201390017

  3. Contents

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
    6. Full Papers
    1. You have free access to this content
  4. Communication

    1. Top of page
    2. Cover Picture
    3. Editorial
    4. Contents
    5. Communication
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    1. Nickel-Catalyzed ortho-Selective Hydrodefluorination of N-Containing Heterocycle-Polyfluoroarenes (pages 873–877)

      Yi He, Zhao Chen, Chun-Yang He and Xingang Zhang

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300327

      Thumbnail image of graphical abstract

      An effective and facile method for preparation of partially fluorinated aromatics via Nickel catalyzed, chelation-assisted ortho selective hydrodefluorination of polyfluoroarnes with triethylsilane has been developed, in which N-containing heterocycles were used as directing groups.

  5. Full Papers

    1. Top of page
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    3. Editorial
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    1. Highly Stereoselective and One-Pot Synthesis of Tetra-substituted Monofluoroalkenes with Aldehydes and Fluorobis(phenylsulfonyl)methane (pages 878–884)

      Xiao Shen, Chuanfa Ni and Jinbo Hu

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300365

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      Highly stereoselective and one-pot synthesis of tetrasubstituted monofluoroalkenes with fluorobis(phenylsulfonyl)methane (FBSM) as the fluoroolefination reagent has been developed. This protocol is amenable to the transformation of non-enolizable aldehydes with less sterically demanding substituents. For enolizable aldehydes and sterically hindered aromatic aldehydes, the reaction furnishes carbonyl addition products.

    2. A General and Highly Selective Method for the Asymmetric Synthesis of Trifluoromethyl-Substituted α- and β-Aminophosphonates (pages 892–900)

      Lijing Wang, Qilong Shen and Long Lu

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300344

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      A highly selective method for the asymmetric formation of trifluoromethyl-substituted α- and β-aminophosphonates was described. The reaction proceeded with high yields and good to excellent diastereoselectivity. The product can be easily converted into corresponding trifluoromethyl-substituted aminophosphoric acids.

    3. Palladium-Catalyzed Cross-Coupling of Fluorinated Vinyl Chlorides with Terminal Alkynes: A General Protocol to Fluorinated Enynes (pages 901–907)

      Sheng Chen, Chunfa Xu, Long Lu and Qilong Shen

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300352

      Thumbnail image of graphical abstract

      An efficient and cost-effective method for the preparation of fluorinated conjugated enynes was described. The method was compatible with a variety of functional groups such as chloride, amine, cyano and ester group. The method could also be extended to the coupling of (R,Z)-3-(2-chloro-1,2-difluorovinyl)-4-alkyloxazolidin-2-one (3) with moderate yields.

    4. Palladium-Catalyzed Intramolecular Fluorooxylation of Styrenes (pages 908–914)

      Zheliang Yuan, Haihui Peng and Guosheng Liu

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300437

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      A palladium-catalyzed intramolecular oxidative fluorooxylation of styrenes has been developed by using NFSI as fluorinating reagent. This reaction provides an efficient way for the synthesis of 2-aryl-3-fluorotetrahydrofuran derivatives.

    5. Copper-Mediated Trifluoromethylation of Terminal Alkynes by S-(Trifluoromethyl)diarylsulfonium Salt (pages 915–920)

      Xiaoping Wang, Jinhong Lin, Chengpan Zhang, Jichang Xiao and Xing Zheng

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300393

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      A convenient method for the trifluoromethylation of a variety of terminal alkynes with S-(trifluoromethyl)diarylsulfoniumtriflate in the presence of copper iodide was described. The reactions proceeded smoothly under mild condition to give the desired product in moderate to good yields.

    6. Nucleophilic Trifluoromethylthiolation of Allylic Bromides: A Facile Preparation of Allylic Trifluoromethyl Thioethers (pages 921–926)

      Jianwei Tan, Guoting Zhang, Yangli Ou, Yaofeng Yuan and Zhiqiang Weng

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300415

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      A facile preparation of allylic trifluoromethyl thioethers was achieved by the reaction of (bpy)Cu(SCF3) with allylic bromides. This protocol afforded the desired trifluoromethylthiolation products in good to excellent yields with high stereo- and regioselectivity. Important functional groups such as alkyl, alkoxy, trifluoromethyl, nitro, halides and geranyl are well tolerated.

    7. Cobalt-catalyzed Selective C[BOND]F Bond Activation and Alkylation of Polyfluoroaryl Imines (pages 927–932)

      Faguan Lu, Hongjian Sun and Xiaoyan Li

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300340

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      C[BOND]F bond activation of polyfluoroaryl imines is explored at cobalt(0) center with an imine-N atom as an anchoring group. It was also found that dialkylation of N-(perfluorobenzylidene)benzenamine with organozinc reagents could be catalyzed by Co(PMe3)4 via C,C-coupling reaction under mild conditions.

    8. Fluorocarbon and Hydrocarbon Benzodioxocycloalkane (C8–C10) End Groups: Effects on Mesomorphism (pages 933–938)

      Wanwan Cao, Peilian Liu, Hongren Chen, Yaohang Zhu, Rihao Chen, Qifang Zhou and Zhuo Zeng

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300286

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      A new class of benzodioxocycloalkane-based (C8–C10) liquid crystals has been prepared. The impact of ring (C8–C10) as end group was investigated. The 8–9 membered ring derivatives, 3a3b, exhibited the nematic phases (N). The mesomorphic behaviors were weakened with increasing the size of the ring. For the ?uorinated medium ring (C8–C10) 3d3f, it was found only the fluorinated ten membered ring 3f showed the LC phases behaviours. Modification of the ring size with different length alkyl groups and variation of the alkyl to polyfluoroalkyl markedly influenced the properties of these compounds.

    9. Radical Addition of Perfluoroalkyl Iodides to Alkenes and Alkynes Initiated by Sodium Dithionite in an Aqueous Solution in the Presence of a Novel Fluorosurfactant (pages 939–944)

      Zhiwei Xiao, Huawei Hu, Jiaoli Ma, Qingyun Chen and Yong Guo

      Version of Record online: 19 JUL 2013 | DOI: 10.1002/cjoc.201300433

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      A new surfactant Cl(CF2)6O(CF2)2SO3N(C2H5)4 was prepared and its properties were measured. The fluorinated surfactant was applied to the fluoroalkylation of perfluoroalkyl iodides with olefins and alkynes. The reactions gave the corresponding adducts in water and avoided the use of organic solvent. The aqueous solution with the surfactant proved to be an effective medium for a radical process.

    10. Copper(I)-Catalyzed Trifluoromethylation of Phthalic Anhydride Derivatives with (Trifluoromethyl)trimethylsilane (pages 945–949)

      Mingxi Wu, Mingjin Wang and Song Cao

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300357

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      An efficient copper-mediated trifluoromethylation of substituted phthalic anhydrides using (trifluoromethyl)trimethylsilane (Me3SiCF3) as a nucleophilic trifluoromethylating reagent in the presence of 1,10-phenanthroline and KF, followed by quenching the reaction mixture with water has been developed. A possible mechanism was suggested.

    11. Regioselective Synthesis of 2,6-Dimethyl-3,5-bis[(3-aryl-5-trifluoromethyl)-isoxazol-4-carbonyl]-pyridine Derivatives (pages 950–954)

      Yindi Yang, Min Zhang, Yiwen Zhu, Li Zhang, Qiqiang Xie, Liping Song and Hongmei Deng

      Version of Record online: 5 JUL 2013 | DOI: 10.1002/cjoc.201300366

      Thumbnail image of graphical abstract

      Cyclization reaction of 2a with aryl imidoyl chlorides 5a5i, derived from chlorination of aryl oximes with N-chlorosuccimide, afforded 2,6-dimethyl-3,5-bis[(3-aryl-5-trifluoromethyl)-isoxazol-4-carbonyl]-pyridine derivatives 6a6i in the presence of base.

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