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  • Yating Zhu, Jinfeng Ling, Lei Li, Xiaohong Guan
    Chinese Chemical Letters. 2020, 31(6): 1545-1549.

    The effects of bisulfite-activated permanganate technology (PM/BS) as a pre-oxidation process on enhancing Microcystis aeruginosa (M. aeruginosa) removal by post coagulation were investigated. The results demonstrated that pretreatment with PM/BS process effectively promoted the algae removal by coagulation with Al2(SO4)3 as the coagulant and this phenomenon was more obvious with the increase of water hardness. Compared to the sole coagulation, PM/BS pre-oxidation combing with coagulation could neutralize the zeta potential of algal cells effectively, decrease the algal cell size, and lead to the formation of more compact flocs due to the in-situ generated MnO2. The effect of oxidant dosages on algal organic matter (AOM) was also studied and no obvious release of macromolecular substances was observed with the dosage of KMnO4 increasing from 3.0 mg/L to 7.0 mg/L, suggesting the integrity of algal cells at a high KMnO4 dosage. Moreover, PM/BS pre-oxidation could lead to the decrease of most analyzed disinfection by-products (DBPs) at a Al2(SO4)3 dosage of 40.0 mg/L. The algae removal efficiency was also significantly enhanced by PM/BS pre-oxidation in the test using real algae-laden water. This study indicated that PM/BS process might be a potential assistant technology for algae removal by subsequent coagulation.

  • Junmei Ye, Runmiao Zhang, Wenjuan Yang, Ying Han, Hao Guo, Ju Xie, Chaoguo Yan, Yong Yao
    Chinese Chemical Letters. 2020, 31(6): 1550-1553.

    Four pillar[5]arene based [3]rotaxanes (1-4) involving two 1,4-diethoxypillar[5]arene (DEP5) rings and a dumbbell-shaped component were successfully synthesized. The dumbbell-shape molecules contain one longer bridge, two triazole sites and two multicomponent stoppers. After threading DEP5 rings with linear guests (G1-G4) which contain two benzaldehyde units, the base catalyzed three-component reaction of dimedone, malononitrile and benzaldehyde was performed to construct the stoppers and connected the pseudorotaxanes with stoppers to generate 1–4. The structures of [3]rotaxanes and their self-assembly behaviors were characterized by 1H NMR, 13C NMR, NOESY, HR-ESI-MS, DLS and TEM technologies. We hope that pillar[5]arene based [3]rotaxanes may have potential applications in drug delivery systems and molecular devices.

  • Meijun Zhu, Ying Han, Changzhou Liu, Weiqing Ma, Chao-Guo Yan
    Chinese Chemical Letters. 2020, 31(6): 1554-1557.

    The 1, 3-dipolar cycloaddition reaction of dimethyl hex-2-en-4-ynedioate with azomethine ylides derived from reaction of L-proline with various isatins in methanol selectively resulted in the formation of functionalized spiro[indoline-3, 3'-pyrrolizine]acrylates as main products and spiro[indoline-3, 3'-pyrrolizine]propiolates as minor products. This result indicated that the electron-deficient alkyne has higher reactivity than that of electron-deficient alkene in 1, 3-dipolar cycloaddition reaction.

  • Fang Wang, Huangdi Feng, Huiqiong Li, Teng Miao, Tiantian Cao, Min Zhang
    Chinese Chemical Letters. 2020, 31(6): 1558-1563.

    Highly active and stable magnetic copper catalysts were successfully achieved by magnetic induced Stöber method and subsequent hydrothermal reaction with copper ions in alkaline condition. The high content of Cu2+ as well as the unique structures of hierarchical copper silicate in the as-prepared catalysts endowed their outstanding catalytic performance. Efficient decarboxylative A3-coupling of α-keto acid, amine and alkyne was realized with the low Fe3O4@CuSiO3 loading. A range of propargylamines were produced in good to excellent yields under solvent-free condition. Moreover, the catalyst can be easily separated from the final organic product with an external magnet. Also, this kind of catalyst could be recycled up to six times while maintaining its activity.

  • Kefeng Wang, Zixi Zhuang, Huihui Ti, Peishan Wu, Xin Zhao, Honggen Wang
    Chinese Chemical Letters. 2020, 31(6): 1564-1567.

    The trans-hydroboration of alkyne represents a challenging task in organic synthesis. Reported herein is an Et2Zn promoted β-trans hydroboration of ynamides by using N-heterocyclic carbene (NHC)-ligated borane as boryl source. The reaction leads to a stereoselective construction of enamides bearing a valuable boryl substituent. Both aromatic and aliphatic ynamides were applicable to the reaction. Synthetic transformation of the C—B bond in the product via Suzuki-Miyaura coupling provides a simple and stereospecific route to multi-substituted enamides. Mechanistic studies were conducted and the possible mechanism was discussed

  • Shuaipeng Lv, Yunfang Sun, Yue Xu, Shihai Yang, Lei Wang
    Chinese Chemical Letters. 2020, 31(6): 1568-1571.

    A Lewis base catalyzed ring expansion of isatin with 2, 2, 2-trifluorodiazoethane (CF3CHN2) is developed. It is characterized that the merge of tetramethylethylenediamine and CF3CHN2 generates reactive triazene intermediates, which construct substituted 3-hydroxy-4-(trifluoromethyl)quinolinones with high efficiency. Synthetic application of the procedure is broadened by 3-trifluormethylpyrazole fused 3-hydroxy-4-(trifluoromethyl)quinolinone synthesis.

  • Yuanqiong Huang, Xueli Lv, Hongjian Song, Yuxiu Liu, Qingmin Wang
    Chinese Chemical Letters. 2020, 31(6): 1572-1575.

    Herein, we report the first RhIII-catalyzed regioselective C8 arylation of quinoline N-oxides with commercially available arylboronic acids as coupling partners. This procedure is simple, and the reaction shows perfect regioselectivity, a broad substrate scope, and isolated yields of up to 92%. We demonstrate the utility of the reaction by using it for late-stage functionalization of a fungicide.

  • Jinjin Zhang, Huiqiao Wang, Yaru Chen, Haiquan Xie, Chenghua Ding, Jiajing Tan, Kun Xu
    Chinese Chemical Letters. 2020, 31(6): 1576-1579.

    Reported herein is the first example of electrochemical selenocyanation of imidazo[1, 5-a]quinolines with KSeCN under metal catalyst- and chemical oxidant-free conditions. This sustainable strategy shows a broad scope and great compatibility with functional groups, and affords synthetically and biologically important selenocyanated imidazo[1, 5-a]quinolines in good to excellent yields with cheap graphite and Ni plates as the electrodes. The gram-scale synthesis was also successfully conducted, which might demonstrate the potential value of this electrochemical protocol.

  • Hao Wu, Nana Ma, Mengxiao Song, Guisheng Zhang
    Chinese Chemical Letters. 2020, 31(6): 1580-1583.

    Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide (DMSO) under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields. This novel transformation is proposed to go through a sequential DMSO-aided Cu insertion into the amide C—N bond, CO extrusion, Cu migration, reductive elimination and DMSO-aided proton migration processes, involving multiple types of bond cleavage and formation in a single chemical step.

  • Jia Chen, Mohammad Chand Ali, Ruirui Liu, Jean Claude Munyemana, Zhan Li, Honglin Zhai, Hongdeng Qiu
    Chinese Chemical Letters. 2020, 31(6): 1584-1587.

    Developing a new type of deep eutectic solvents (DESs) is indispensable for expanding their application in various fields. Here, we report a series of new highly basic DESs. FT-IR, quantitative 1H NMR, MD simulation and physical properties show that these basic liquids are made up of hydroxide acceptor of alkali metal hydroxides in which the hydrogen bonding interactions coordinate the donor. These DESs can be played three roles as new solvents, template and reactant for facile and ultra-fast preparation of transition metal oxide nanomaterials such as NiCo2O4, MnCo2O4, NiMn2O4, CoCu2O4 and Co3O4 under mild condition. This work shows one of the low energy-intensive methods for nanomaterial preparation. These initial findings of basic deep eutectic solvents provide a potential applicability around the systematic development of transition metal oxide nanosheets.

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