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Key progresses of MOE key laboratory of macromolecular synthesis and functionalization in 2022

Chinese Chemical Letters 2024年第3期35卷 114-126页

作者： Xumeng Deng Kaihao Chen Kai Pang Xiaoting Liu Minsong Gao Jie Ren Guanwen Yang Guangpeng Wu Chengjian Zhang Xufeng Ni Peng Zhang Jian Ji Jianzhao Liu Zhengwei Mao Ziliang Wu Zhen Xu Haoke Zhang Hanying Li MOE Key laboratory of Macromolecular synthesis and Functionalization International Research Center for X PolymersDepartment of Polymer Science and EngineeringZhejiang UniversityHangzhou 310027China

In 2022,The MOE Key laboratory of Macromolecular synthesis and Functionalization in Zhejiang University had achieved several important ***,a series of well-defined dinuclear organoboron catalysts were developed to precisely control the enchainment of ether and carbonate segments during the copolymerization of CO_(2)and ***,polyester had been synthesized through cationic copolymerization of cyclic ***,ring-opening polymerization of carbon dioxide based valerolactone had been achieved,revealing the prospect of 3-ethylidene-6-vinyltetrahydro-2H-pyran-2-one(EVL)in utilizing CO_(2)and synthesizing functional ***,machine learning methods have been applied to biomaterial research,enabling high-throughput screening of functional biomaterial surfaces for implantable devices,and searching for potent antimicrobial peptides in whole combinatorial peptide ***,methods of characterization of biomacromolecule RNA transcription and manipulation of nucleoside modification were ***,artificial enzymes-armed Bifidobacterium Longum probiotics were established to tune down gut ***,three-dimensional(3D)printing technologies were used to engineer tough supramolecular ***,hydroplastic foaming graphene frameworks for acoustic and conductive polymer composites were provided for ***,aggregate photophysics about the nature of through-space interactions(TSIs)and manipulating their strength in small molecules with non-conjugated structure had been ***,the forming mechanism of a newfound nested texture in poly(L-lactic acid)(PLLA)spherulitic films had been ***,the isotropically dyeing mechanism of KDP single crystals grown from hydrogels have been *** related works are reviewed in this paper.

关键词： Polymer Catalyst Biomaterial research mRNA Hydrogel Graphene Crystal

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S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds

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Chinese Chemical Letters 2024年第5期35卷 151-154页

作者： Ze-Yuan Ma Mei Xiao Cheng-Kun Li Adedamola Shoberu Jian-Ping Zou Key laboratory of organic synthesis of Jiangsu Province College of Chemistry and Chemical EngineeringSoochow UniversitySuzhou 215123China

An efficient synthesis of the electrophilic reagent,S-(1,3-dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate(SDDP)is ***,the synthetic applications of SDDP wherein the transfer of the SP(O)(OEt)_(2) moiety occurs were *** this manner,SDDP underwent facile SP(O)(OEt)_(2) transfer with electron-rich substrates such as ketones,indoles,and thiols to formα-phosphorothiolated ketones,3-phosphorothiolated indoles and S-phosphorothiolated thioethers,respectively.

关键词： Electrophilic reagent Phosphorothiolation Electrophilic substitution

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Cobalt(Ⅲ)hydride HAT mediated enantioselective intramolecular hydroamination access to chiral pyrrolidines

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Science China Chemistry 2024年第6期67卷 2002-2008页

作者： Qi Meng Tao Qin Huanran Miao Ge Zhang Qian Zhang Jilin Province Key laboratory of organic Functional Molecular Design&synthesis Department of ChemistryNortheast Normal UniversityChangchun130024China State Key laboratory of Organometallic Chemistry Shanghai Institute of Organic ChemistryChinese Academy of SciencesShanghai200032China

Enantioenriched pyrrolidines and derivatives are ubiquitous substructures in compounds of importance to medicinal and biological ***,we report an efficient cobalt-catalyzed intramolecular asymmetric hydroamination reaction that produces chiral pyrrolidines with good to excellent yield and *** with previously reported radicalinvolved methodologies for enantioenriched pyrrolidines,these conditions feature two elegant versatilities,enabling(1)the use of cobalt-catalyzed hydrogen atom transfer(HAT)to generate organocobalt intermediates that bring radical reaction to organometallic chemistry,and(2)enantioselective intramolecular C-N bond forging through an S_(N)2-like displacement involving dynamic kinetic resolution(DKR).This approach provides a new alternative and efficient methodology for enantioselective radical-involved C-N bond construction that can be used in the synthesis of both chiral pyrrolidines and homologous nitrogen heterocycles.

关键词： asymmetric catalysis radical hydroamination cobalt catalysis hydrogen atom transfer

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Visible Light-Induced[3+2]Annulation Reaction of Alkenes with Vinyl Azides:Direct synthesis of Functionalized Pyrroles

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Chinese Journal of Chemistry 2024年第2期42卷 151-156页

作者： Ming Yang Xin-Yu Wang Jie Wang Yu-Long Zhao Jilin Province Key laboratory of organic Functional Molecular Design&synthesis Faculty of ChemistryNortheast Normal UniversityChangchunJilin 130024China

A photocatalytic[3+2]annulation of alkenes with vinyl azides was developed under irradiation by visible light in the presence of organic dye *** substrate scope and high functional group tolerance were demonstrated by more than 50 *** reaction provides a novel and efficient method for the synthesis of polyfunctionalized pyrroles under very mild metal-free conditions without other additives.

关键词： Photocatalysis Vinyl azides Alkenes Pyrroles Annulation Radical reactions

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Cycloaddition Reactions of Epoxides and CO_(2)Catalyzed by Bifunctional Rare-Earth Metal Complexes Bearing Amino-Bridged Tris(phenolato)Ligands

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Chinese Journal of Chemistry 2024年第14期42卷 1571-1581页

作者： Yongjie Chen Yanwei Wang Jun Nong Dan Yuan Yingming Yao Key laboratory of organic synthesis of Jiangsu Province College of ChemistryChemical Engineering and Materials ScienceDushu Lake CampusSoochow UniversitySuzhouJiangsu215123 China

Eight zwitterionic rare earth metal complexes stabilized by amino-bridged tris(phenolato)ligands bearing quaternary ammonium side-arms were synthesized and *** complexes were used as single-component catalysts for the cycloaddition of CO_(2)and epoxides,and their catalytic activities are obviously higher than those of their binary *** studies revealed that the halide anions(Cl^(–),Br^(–),I^(–))and the metal complexes influenced the catalytic activity,and the lanthanum complex bearing iodide anion showed the highest catalytic activity for this addition reaction.A variety of mono-substituted epoxides were converted to cyclic carbonates in good to excellent yields(55%—99%)with high selectivity(>99%)at 30℃and 1 bar CO_(2),whereas internal epoxides required higher both reaction temperatures(60—120℃)and catalyst loading(2 mol%)for high *** catalyst was recyclable for four times without noticeable loss of catalytic *** on the results of kinetic studies and in℃situ IR reactions,a plausible reaction mechanism was proposed.

关键词： Bifunctional catalyst Carbon dioxide Cyclic carbonate Rare-earth metal Tris(phenolato)ligand Insertion Cycloaddition C1 building blocks

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Integrating Bimetallic Nanoparticles with Covalent organic Frameworks as Multifunctional Nanozyme for Colorimetric Detection of Hydrogen Peroxide and Glutathione

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Journal of Analysis and Testing 2024年第03期8卷 278-287页

作者： Yuying Yuan Xiaoxue Xi Ting Bao Pingguan Bian Feng Pei Xiuhua Zhang Shengfu Wang Wei Wen Collaborative Innovation Center for Advanced organic Chemical Materials Co-constructed by the Province and Ministry of Education Key Laboratory for the Synthesis and Application of Organic Functional MoleculesCollege of Chemistry and Chemical EngineeringHubei University Hubei Yihua Chemical Co. Ltd

The controllable growth of metal nanoparticles on nanomaterials is becoming an effective strategy for developing nanocomposites with designated performance. Herein, a simple and mild strategy for the in situ growth of Pt–Pd bimetallic nanoparticles on covalent organic frameworks（COFs） to regulate the nanozyme activity was designed for colorimetric detection of hydrogen peroxide（H2O2） and glutathione（GSH）. The COFs not only offer sufficient loading sites for the uniform dispersion of Pt–Pd bimetallic nanoparticles, but also increase the adsorption of substrate to promote the catalytic reaction. With the bimetallic synergistic effect of Pt–Pd nanoparticles, the prepared multifunctional nanozyme（Pt–Pd/COFs nanozyme） simultaneously exhibited superior peroxidase（POD）-like activity and oxidase（OXD）-like activity. Using the multifunctional nanozyme, a colorimetric sensing system was constructed for sensitive detection of H2O2and GSH, with the wide linear ranges of 5–1000 μmol/L and 1–40 μmol/L, and the detection limits were 1.14 μmol/L and 0.43 μmol/L, respectively. It was successfully used for the detection of real samples in environmental water and serum, providing a simple method for disease diagnosis and environmental monitoring.

关键词： Bimetallic synergistic effect H2O2 and GSH detection Oxidase-like activity Peroxidase-like activity Pt–Pd/COFs nanozyme

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Palladium(Ⅱ)-Catalyzed Markovnikov Hydroalkynylation of Unactivated Terminal Alkenes

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Chinese Journal of Chemistry 2024年第1期42卷 29-34页

作者： Chuanqi Hou Pinhong Chen Guosheng Liu Sstate Key laboratory of Organometallic Chemistry and Shanghai Hongkong Joint Laboratory in Chemical SynthesisCenter for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai 200032China Chang-Kung Chuang Institute East China Normal UniversityShanghai 200062China

Alkynes are versatile synthons in organic synthesis,as well as important structural moieties in bioactive ***,transition metal-catalyzed hydroalkynylation of alkenes has been developed with reactive alkenes and alkenes bearing directing ***,the regioselective hydroalkynylation of simple alkenes is still ***,we have developed a palladium-catalyzed Markovnikov hydroalkynylation of unactivated terminal alkenes,which provides an efficient approach for the synthesis of branched alkynyl compounds under mild *** reaction features excellent functional group tolerance,good reaction yields and excellent ***,the asymmetric hydroalkynylation reaction has also been achieved with moderate enantioselectivity by introducing a sterically bulky chiral Pyox ligand.

关键词： Palladium catalysis Alkynylpalladation Unactivated terminal alkenes Markovnikov hydroalkynylation

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S-,P-stabilized bromoallenes for modular allenylborylation of alkenes

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Science China Chemistry 2024年第1期67卷 360-367页

作者： Jixin Wang Donghao Luo Ying Hu Zhili Duan Jianlin Yao Konstantin Karaghiosoff Jie Li Key laboratory of organic synthesis of Jiangsu Province Suzhou Key Laboratory of Pathogen Bioscience and Anti-infective MedicineCollege of ChemistryChemical Engineering and Materials ScienceSoochow UniversitySuzhou 215123China Department Chemie Ludwig-Maximilians-Universitat MunchenButenandtstr.5-13Haus F81377 MunichGermany State Key laboratory and Institute of Elemento-organic Chemistry Haihe Laboratory of Sustainable Chemical TransformationsCollege of ChemistryNankai UniversityTianjin 300071China

Simultaneously forming a carbon-carbon and a carbon-heteroatom bond in a single step through transition metal-catalyzed alkene difunctionalization strategy has emerged as a powerful tool for synthetic organic *** to the uncontrollable reactivity,direct cross-coupling with bromoallenes as the building blocks for the selective allenation and borylation remains *** herein report a new type of S-and P-stabilized bromoallenes for palladium-catalyzed modular allenation and borylation of alkenes to the divergent synthesis of multiply functionalized allenes in a highly regio-and diastereoselective *** reaction features broad substrate scope and wide functional group compatibility,thus providing a straightforward method to install allenyl and boryl groups across *** experiments highlight the crucial importance of S-,P-stabilization for the oxidative insertion of Pd-species into the allenyl-Br *** facile syntheses of bioactive allenic steroids and exocyclic allenes demonstrate the synthetic utility of this protocol.

关键词： alkene difunctionalization olefins bromoallenes allenylborylation palladium

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Atomic-resolution Interfacial Microstructure and Thermo-electro-magnetic Energy Conversion Performance of Gd/Bi0.5Sb1.5Te3 Composites

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Energy & Environmental Materials 2024年第4期7卷 355-363页

作者： Chengshan Liu Wenjie Xu Ping Wei Shaoqiu Ke Wenjun Cui Longzhou Li Dong Liang Xianfeng Ye Tiantian Chen Xiaolei Nie Wanting Zhu Wenyu Zhao Qingjie Zhang State Key laboratory of Advanced Technology for Materials synthesis and Processing Wuhan University of Technology Foshan Xianhu laboratory of the Advanced Energy Science and Technology Guangdong laboratory

Thermo-electro-magnetic materials with simultaneously large magnetocaloric(MC) and thermoelectric (TE) effects are the core part for designing TE/MC all-solid-state cooling *** MC phase with TE material is an effective ***,the elemental diffusion and chemical reaction occurring at the two-phase interfaces could significantly impair the cooling performance.

关键词： interfacial reaction magnetocaloric performance thermoelectric performance thermo-electro-magnetic materials

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Copper Catalyzed Enantioconvergent Nucleophilic Substitutions

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Chinese Journal of Chemistry 2024年第10期42卷 1161-1174页

作者： Chunxi Huang Zilong Wan Aoping Zhu Caiyou Chen College of Chemistry and Molecular Sciences Wuhan UniversityWuhanHubei 430072China Ministry of Education Key laboratory for the synthesis and Application of organic Functional Molecules and College of Chemistry and Chemical Engineering Hubei UniversityWuhanHubei 430062China

As a versatile earth-abundant transition metal,Cu has long been widely applied in the C—C and C—X bond forming *** for now,low-valent Cu(Ⅰ)is known to reduce the redox active electrophiles via an SET pathway to give the corresponding radical and Cu(Ⅱ)*** resulting Cu(Ⅱ)species can interact with the radical via the out-sphere pathway,affording the coupling ***,Cu(Ⅱ)can trap the radical through the inner-sphere process to generate Cu(Ⅲ)species and then realize challenging bond formations due to the facile reductive elimination of Cu(Ⅲ)*** copper catalysis has been widely applied in arylations of various nucleophiles,copper-catalyzed enantioconvergent nucleophilic substitutions of racemic alkyl electrophiles have been less explored,likely due to the difficulties in overcoming the reduction potential of alkyl electrophiles,elimination of side reactions,and enantiomeric *** order to overcome the high reduction potential of alkyl electrophiles,the photo-induced strategy has been developed under mild *** alternative strategy with new anionic tridentate ligands has also been reported in this *** review summarizes recent developments in copper-catalyzed enantioconvergent nucleophilic substitutions of alkyl electrophiles by various nucleophiles to realize C—N,C—C,C—B,C—P and C—O bond formations and their brief mechanistic studies.

关键词： Enantioconvergent Nucleophilic substitution Copper Radical reactions Photocatalysis Asymmetric catalysis

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