Chinese Journal of Chemistry

Cover image for Vol. 32 Issue 10

Special Issue: Dedicated to Professor Chengye Yuan and Professor Li-Xin Dai on the occasion of their 90th birthdays (II)

October, 2014

Volume 32, Issue 10

Pages 925–1082

  1. Cover Picture

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Reviews
    5. Communications
    6. Full Papers
    7. Note
    1. You have free access to this content
      Cover Picture: A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o-Quinone Methides Generated from 2-(1-Tosylalkyl)phenols (Chin. J. Chem. 10/2014) (page 925)

      Bo Wu, Xiang Gao, Mu-Wang Chen and Yong-Gui Zhou

      Article first published online: 14 OCT 2014 | DOI: 10.1002/cjoc.201490022

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      The cover picture shows a concise synthesis of 2-(2-hydroxyphenyl)acetonitriles through reaction of 2-(1-tosylalkyl)phenols and trimethylsilyl cyanide in the presence of base potassium carbonate and tetra-n-butylammonium fluoride (TBAF). 2-(1-Tosylalkyl)phenols generate ortho-quinone methides (o-QM) intermediates under the basic conditions and TBAF serves as an initiator to deliver cyanide anion. Subsequently, o-QM intermediates undergo Michael addition with the cyanide anion to furnish 2-(2-hydroxyphenyl)acetonitriles. Additionally, the adduct 2-(2-hydroxyphenyl)acetonitriles can be conveniently transformed to benzofuranones. This methodology features good yields and the products can be further functionalized. More details are discussed in the article by Zhou et al. on page 981–984.

  2. Contents

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Reviews
    5. Communications
    6. Full Papers
    7. Note
    1. Contents: Chin. J. Chem. 10/2014 (pages 927–934)

      Article first published online: 14 OCT 2014 | DOI: 10.1002/cjoc.201490023

  3. Reviews

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Reviews
    5. Communications
    6. Full Papers
    7. Note
    1. Recent Advances of the Combination of Au/Acid Catalysis (pages 937–956)

      Shuo Zhang, Fang Wei, Chuangling Song, Jiong Jia and Zhenghu Xu

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400428

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      The combination of a gold catalyst with another acid catalyst, including Bronsted acid and Lewis acid, is possible to bring two distinctive catalytic systems together and deliver unprecedented new reactions. The recent progress in the Au/Acid relay catalysis was reviewed.

    2. Recent Research Developments of Perovskite Solar Cells (pages 957–963)

      Yingzhuang Ma, Shufeng Wang, Lingling Zheng, Zelin Lu, Danfei Zhang, Zuqiang Bian, Chunhui Huang and Lixin Xiao

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400435

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      The perovskite-based inorganic-organic hybrid solar cells outrush as a superstar for solar power conversion. In this review, we summarized the recent development of this photovoltaic device. The materials, fabrication methods, charge transfer properties, stabilities, and microscopic mechanism are discussed. The outlook for future study and application is also given.

    3. Tau Protein Associated Inhibitors in Alzheimer Disease (pages 964–968)

      Qian-Qian Li, Ting-Ting Chu, Yong-Xiang Chen and Yan-Mei Li

      Article first published online: 8 OCT 2014 | DOI: 10.1002/cjoc.201400469

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      Several types of tau protein inhibitors: reducing tau aggregation, decreasing tau phosphorylation and inducing tau O-GlcNAcylation.

  4. Communications

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Reviews
    5. Communications
    6. Full Papers
    7. Note
    1. A Highly Enantioselective Mannich-Type Reaction of Glycine Schiff Base Catalyzed by a Cinchoninium Salt (pages 969–973)

      Zhonglin Tao, Arafate Adele, Xiang Wu and Liuzhu Gong

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400453

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      A chiral phase-transfer catalyst, derived from the combination of cinchona alkaloid backbone and BINOL skeleton, enabled a Mannich reaction of glycine Schiff base with N-Boc-imines to generate α,β-diamino acid derivatives in excellent yields (up to 99%) and with high diastereoselectivities (up to >0:1) and enantioselectivities (up to 96% ee).

    2. Palladium-Catalyzed 2H-1,2,3-Triazole-Directed Oxidative Alkoxylation of Arenes with Alcohols (pages 974–980)

      Wenjuan Shi and Zhangjie Shi

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400462

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      A palladium catalyzed ortho-alkoxylation of aryl C[BOND]H bond with alcohols was described. Trizaole was used as new directing group. A series of functional groups could be tolerated and the reaction is not sensitive to moisture and air.

    3. A Concise Synthesis of 2-(2-Hydroxyphenyl)acetonitriles via the o-Quinone Methides Generated from 2-(1-Tosylalkyl)phenols (pages 981–984)

      Bo Wu, Xiang Gao, Mu-Wang Chen and Yong-Gui Zhou

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400463

      Thumbnail image of graphical abstract

      A concise synthesis of 2-(2-hydroxyphenyl)acetonitriles has been developed through reaction of trimethylsilyl cyanide and the o-quinone methides in situ generated from 2-(1-tosylalkyl)phenols under basic conditions. In addition, 2-(2-hydroxyphenyl)acetonitriles could be conveniently transformed to benzofuranones.

    4. Asymmetric Hydrogenation of 2-Aryl-5,6-dihydropyrazine Derivatives with Chiral Cationic Ruthenium Diamine Catalysts (pages 991–994)

      Yong Li, Yanmei He, Fei Chen and Qinghua Fan

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400422

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      The first asymmetric hydrogenation of 5,6-dihydropyrazines catalyzed by chiral cationic Ru-diamine complex (R,R)-1a was developed, affording chiral piperazine derivatives with good enantioselectivities (up to 89% ee).

    5. Synthesis and Surface Activity Study of a Novel Branched Fluorinated Anion Surfactant with CF3CF2CF2C(CF3)2 Group (pages 995–998)

      Min Sha, Renming Pan, Lewu Zhan, Ping Xing and Biao Jiang

      Article first published online: 8 OCT 2014 | DOI: 10.1002/cjoc.201400377

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      A novel branched fluorinated anion surfactant 4-(3,3,4,4,5,5,5-heptafluoro-2,2-bis-trifluoromethyl-pentyl)-benzene lithium phosphonate was successfully synthesized via a four-step route using perfluoro-2-methyl-2-pentene as starting material. The surface activity was investigated. The result showed that the cmc value of the surfactant in water is about 1.5×10−2 mol/L at 298 K and the surface tension of the aqueous solution is 19.2 mN/m at the cmc.

    6. Co2(CO)8-mediated Selective Reductions of Propargyl Alcohol Derivatives to Alkenes (pages 999–1002)

      Ying Dou, Ping Xing, Zuogang Huang and Biao Jiang

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400396

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      In the presence of Co2(CO)8 and additives, propargyl alcohol derivatives could be reduced to alkenes in moderate to good yield. The selectivity of this reaction could be controlled by adding different additives: with H2O as the additive, the major configuration of product is Z-alkene; with CF3COOH as the additive, the major configuration of product is E-alkene.

    7. Asymmetric Pudovik Reaction of Chiral Fluoroalkyl α,β-Unsaturated Ketimines and Diphenyl Phosphite (pages 1003–1006)

      Peng Li, Min Jiang and Jin-Tao Liu

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400419

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      A series of fluoroalkylated α-amino phosphonates were successfully synthesized from the Pudovik reactions of chiral ?uoroalkyl α?β-unsaturated N-tert-butanesul?nyl ketimines derivated from (R)-tert-butanesulfinamide in good yields with high diastereoselectivities under mild conditions.

    8. Two New Triterpenoids from Lycopodium japonicum Thunb. (pages 1007–1010)

      Xiaojing Wang, Dequan Yu and Shishan Yu

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400456

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      Two new serratene-type triterpenoids were isolated from Lycopodium japonicum Thunb. along with eight known ones. Their structures were elucidated on the basis of extensive spectroscopic analysis.

    9. Light Induced Inhibition of Protein Phosphatase Calcineurin (pages 1011–1014)

      Andres Quintero, Weilin Lin, Sophia Hermann and Yixin Zhang

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400432

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      A photo induced covalent inhibitor has been discovered for protein phosphatase calcineurin, the target of immunosuppressive drugs cyclosporin and tacrolimus.

  5. Full Papers

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Reviews
    5. Communications
    6. Full Papers
    7. Note
    1. Design, Synthesis, Photophysical Studies and Electrochemistry of Carbazole-, Oxadiazole-, and Oxadiazole-Triarylamine-Containing Rhenium(I) Diimine Alkynyl Complexes (pages 1015–1021)

      Wai-Kin Chung, Keith Man-Chung Wong and Vivian Wing-Wah Yam

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400442

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      A series of rhenium(I) diimine alkynyl complexes with various electron- and hole-transporting moieties has been synthesized and characterized. Their electronic absorption, emission and electrochemical properties have also been studied.

    2. Minimum Amount of Extracting Solvent of (A1A2···At−1)/(A2A3···At) Separation When Using Non-barren Extracting Solvent (pages 1022–1028)

      Fu-Xiang Cheng, Sheng Wu, Song-Ling Wang, Bo Zhang, Yan Liu, Chun-Sheng Liao and Chun-Hua Yan

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400475

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      Minimum amounts of extracting solvent and scrubbing agent solution (Smin and Wmin) should correspond to the S and W causing that the impurities just disappear in the final raffinate and extract respectively, while ASIR of some continuous stages around the feed stage (stage 134) has a same value of 1. The present article concluded that it has no influence upon Smin and Wmin required for a given (A1A2···At−1)/(A2A3···At) separation whether the employed extracting solvent and scrubbing agent solution are barren or not. Additionally at the aqueous outlet, the exiting flowrate of each component equals to the sum of the flowrate of this component from the feed and that entering stage 1 together with the extracting solvent, and this is also the case at the organic outlet.

    3. A Novel Self-Penetrated Framework with New Topology Based on Rigid Ligands (pages 1029–1032)

      Guangxun Lyu, Qihui Chen, Feilong Jiang, Kang Zhou, Kongzhao Su, Lian Chen, Daqiang Yuan and Maochun Hong

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400425

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      A novel coordination polymer based on rigid ligands has been synthesized and structurally characterized, which exhibits a new 3D self-penetrated framework with new topology, while their fluorescent properties were also studied.

    4. Synthesis and Structure of Azacalix[2]pyrimidine[2]triazines and Their Self-assembly in the Solid State (pages 1033–1038)

      Lixia Wang, Dexian Wang and Meixiang Wang

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400505

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      In the presence of different additives during the growth of single crystals, self complementary azacalix[2]pyrimidine[2]triazines containing amino (-NH2) groups gave varied self-assembled structures due to the formation of different intermolecular hydrogen bond motifs.

    5. Efficient and Practical Syntheses of Enantiomerically Pure (S)-(−)-Norcryptostyline I, (S)-(−)-Norcryptostyline II, (R)-(+)-Salsolidine and (S)-(−)-Norlaudanosine via a Resolution-Racemization Method (pages 1039–1048)

      Ruiheng Zhu, Zhangli Xu, Wei Ding, Shiling Liu, Xiaoxin Shi and Xia Lu

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400471

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      The enantiomerically pure tetrahydroisoquinolines (S)-(−)-norcryptostyline I [(S)-(−)-1], (S)-(−)-norcryptostyline II [(S)-(−)-2], (R)-(+)-salsolidine [(R)-(+)-3] and (S)-(−)-norlaudanosine [(S)-(−)-4] were obtained in 45%, 40%, 41% and 38% yields, respectively, via resolution of the racemic compounds (RS)-(±)-14. In addition, the compounds (R)-(+)-1, (R)-(+)-2, (S)-(−)-3 and (R)-(+)-4 from the mother liquors were efficiently racemized via a one-pot redox method in almost quantitative yields.

    6. Synthesis of PAA-g-PNVCL Graft Copolymer and Studies on Its Loading of Ornidazole (pages 1049–1056)

      Wenhao Qian, Peicheng Xu, Guolin Lu and Xiaoyu Huang

      Article first published online: 8 OCT 2014 | DOI: 10.1002/cjoc.201400472

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      A well-defined graft copolymer, poly(tert-butyl acrylate)-g-poly(N-vinylcaprolactam) (PtBA-g-PNVCL), was synthesized by successive reversible addition-fragmentation chain transfer (RAFT) polymerization and atom transfer radical polymerization (ATRP) started from a new acrylate monomer, tert-butyl 2-((2-chloropropanoyloxy)methyl)acrylate. The hydrophobic PtBA backbone was selectively hydrolyzed without affecting PNVCL side chains in acidic surrounding to provide PAA-g-PNVCL graft polymer. The double-hydrophillic copolymer PAA-g-PNVCL was used to load ornidazole (ONZ) by physical entrapping. Drug release experiment of the ONZ-loaded micelles indicated the pH-dependent drug release characteristics.

    7. Tuning the Charge Transport Property of Naphthalene Diimide Derivatives by Changing the Substituted Position of Fluorine Atom on Molecular Backbone (pages 1057–1064)

      Xiao Zhang, Zhongli Wang, Shiyan Chen, Zheng Zhao, Wei Yuan, Huaping Wang and Xike Gao

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400488

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      Three naphthalene diimide derivatives fused 2-(1,3-dithiol-2-ylidene)-2-fluorophenylacetonitrile moieties were synthesized and their charge transport properties were tuned by changing the position of fluorine atom on the phenyl group.

    8. Two Cluster-Based Coordination Polymers Derived from [Et4N][Tp*WS3(CuBr)3] and CuCN: Isolation, Structures and Amplified Third-Order Nonlinear Optical Responses (pages 1065–1071)

      Quan Liu, Wenhua Zhang, Zhenrong Sun and Jianping Lang

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400412

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      Two coordination polymers [Tp*WS3Cu3(µ3-DMF)(CN)3Cu]2·2DMF (2·2DMF, 2D network) and [Tp*WS3Cu3(µ3-DMF)(CN)3Cu(α-tolunitrile)]2·3MeCN (3·3MeCN, 1D ladder chain) were isolated from the reaction of a W/Cu/S precursor [Et4N][Tp*WS3(CuBr)3] (1) with three equiv. of CuCN in DMF/MeCN/benzonitrile or DMF/MeCN/α-tolunitrile mixed solvents. The third-order nonlinear optical responses of 2 and 3 in DMF were 10 times augmented compared to those of the precursor 1.

    9. In Situ Preparation of Au-SH@SO3H-SBA-15 Catalyst with Enhanced Activity and Durability in Alkyne Hydration (pages 1072–1076)

      Fengxia Zhu and Hexing Li

      Article first published online: 15 SEP 2014 | DOI: 10.1002/cjoc.201400408

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      A novel bifunctional Au-SH@SO3H-SBA-15 catalyst was synthesized through in situ reduction of Au3+ with SH-SBA-15. Au nanoparticles of the catalyst were formed with uniformed, narrow size distribution around 1–2 nm. The catalyst for water-medium alkyne hydration displayed higher efficiencies than its homogeneous catalysts. The robust catalyst could be easily recycled and used repetitively at least 9 times without significant loss of catalytic efficiency.

  6. Note

    1. Top of page
    2. Cover Picture
    3. Contents
    4. Reviews
    5. Communications
    6. Full Papers
    7. Note
    1. Extraction and Separation of Rare Earths from Nitrate Medium by Mixtures of p-Phosphorylated Calixarene and 1-Phenyl-3-methyl-4-benzoyl-pyrazalone-5 (pages 1077–1082)

      Youcai Lu, Yanling Li, Yanfeng Bi and Wuping Liao

      Article first published online: 29 SEP 2014 | DOI: 10.1002/cjoc.201400470

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      The mixtures of p-phosphorylated calixarene (L) and HPMBM exhibit synergistic effects on the gadolinium(III) extraction from nitrate medium.

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