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Trifunctionalization of Aryl Iodides with Two Distinct Nitrogen and Carbon Electrophiles by Palladium/Norbornene Catalysis

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Chinese Journal of Chemistry 2021年第10期39卷 2659-2667页

作者： Jing Wang Hui Wang Zihan Wang Linqiang Li Cheng Qin Xinjun Luan Key Laboratory of Synthetic and Natural Functional Molecule of the Ministry of Education College of Chemistry&Materials ScienceNorthwest UniversityXi'anShaanxi710127 China

Main observation and conclusion Herein,we report a highly chemo-and regioselective vicinal trifunctionalization of aryl iodides by palladium/Norbornene(Pd/NBE)catalysis.The key feature of this new method is the introduction of two distinct nitrogen and carbon electrophiles,with a large gap in reactivity,for ortho-unsubstituted aryl iodides via an intermolecular and intramolecular C―H functionalization,respectively.Eight types of ipso terminations can be coupled with both ortho-amination and ortho-alkylation,affording a variety of polysubstituted benzoheterocyclic scaffolds.Silicon-tethered substrates can lead to polyfucntional arenes via a single-step operation.Noteworthy,these products exhibit full-color-tunable strong fluorescence emissions with large Stokes shifts,and product 7r can serve as a fluorescent probe to specifically target lysosome in living cells.

关键词： Trifunctionalization C-H activation Polyfunctional arenes Norbornene Palladium

Quinolinyl Imidazolidin-2-imine Nickel Catalyzed Efficient Copolymerization of Norbornene with para-Chlorostyrene

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Chinese Journal of Polymer Science 2020年第9期38卷 941-949,I0005页

作者： Yan-Qing Li Jian Zhou Ru Xiao Zheng-Guo Cai State Key Laboratory for Modification of Chemical Fibers and Polymer Materials College of Material Science and EngineeringDonghua UniversityShanghai 201620China College of Biological and Chemical Engineering Guangxi University of Science and TechnologyLiuzhou 545006China

A series of novel quinolinyl imidazolidin-2-imine nickel complexes with different substituents on the imidazolidin-2-imine ligand were synthesized and characterized.The complexes in the presence of methylaluminoxane(MAO)as a cocatalyst catalyzed the copolymerization of Norbornene(N)and styrene(S)or para-chlorostyrene(CS)with high activity(up to 1070 kg·mol^-1·h^-1).The installation of sterically bulky substituents on the imidazolidine-2-imine ligand was effective for the increase of the molecular weight and the comonomer content,affording high molecular weight copolymers with tunable CS content(0.57 mol%-11.7 mol%),in which the existence of CI group can provide reaction site for the further functionalization of copolymers as well as the synthesis of graft or cross-linked polymers.The linear relationship between the comonomer content and the glass transition temperature of the copolymers and the monomer reactivity ratios in the copolymerization indicated the formation of the expected functionalized cyclic olefin copolymers(COC).

关键词： Imidazolidin-2-imine ligand Nickel complex Norbornene para-Chlorostyrene Copolymerization

Efficient Addition Polymerization of Norbornene with Polar Norbornene Derivatives by Neutral Nickel(Ⅱ) Catalysts

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Chinese Journal of Polymer Science 2019年第12期37卷 1215-1223,I0005页

作者： Ling Guo Yan-Ping Zhang Hong-Liang Mu Li Pan Kai-Ti Wang Huan Gao Bin Wang Zhe Ma Yue-Sheng Li Tianjin Key Lab of Composite&Functional Materials School of Material Science and EngineeringTianjin UniversityTianjin UniversityTianjin 300350China Changchun Institute of Applied Chemistry Chinese Academy of SciencesChangchun 130022China School of Materials Science and Engineering Chongqing University of TechnologyChongqing 400054China Collaborative Innovation Center of Chemical Science and Engineering(Tianjin) Tianjin 300072China

A series of nickel complexes{4 a:[(2,6-iPr2C6H3)N=CHC16H12O]Ni(Me)(Py),4b:[(2,6-iPr2C6H2OCH3)N=CHC16H12O]-Ni(Me)(Py),4 c:[(2,6-iPr2C6H2Cl)N=CHC16H12O]Ni(Me)(Py),and 4d:[(2,6-iPr2C6H2CF3)N=CHC16H12O]Ni(Me)(Py)}based onβ-ketiminato ligands bearing various electron-donating or electron-withdrawing substituents on the para-position of the aniline group were synthesized and unambiguously characterized.The X-ray crystallographic analysis showed that complexes 4 b and 4 d adopted a nearsquare-planar geometry,and the anilines bearing a para-OMe or―CF3 group were found to situate on the axial position of the metal center.All complexes exhibited high activities up to 1.25×10^7–1.35×10^7 g PNB·molNi^–1·h^–1 toward Norbornene(NBE)addition polymerization(conversion>91.2%in 2 min)under low loading of B(C6F5)3(B/Ni=3)at 30°C,affording polymers with high molecular weight up to 2.54×10^6–3.18×10^6.Different levels of decrease in catalytic activities could be observed for all catalysts as the reaction temperature increased;4 d bearing a strong electron-withdrawing―CF3 group showed the highest activity at 70°C,while others exhibited notable decrease in catalytic activity with the raise in reaction temperature.Complexes 4 a–4 d showed remarkable tolerance to polar groups and could efficiently promote the copolymerization of NBE with its polar derivatives,including NBE bearing small acetate and hydroxyl group,as well as bulky oligomers,yielding copolymers with high functional NBE incorporations.Novel NBE copolymers with high functional comonomer incorporations and improved solubility were obtained in high yields.

关键词： Neutral nickel catalysts Norbornene Norbornene derivatives Vinyl-type polymerization

Synthesis, Crystal Structure and Norbornene Polymerization of a Palladium(Ⅱ) Complex Based on Phenoxyimine Ligand

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Chinese Journal of Structural Chemistry 2019年第2期38卷 293-300,168页

作者：毛敏捷余锦发李慧萍周贤波简丽菊张丹丹林美君陈建新张治纯 College of Chemistry and Materials Science Fujian Normal University State Key Laboratory of Structural Chemistry Fujian Institute of Research on the Structure of Matter Chinese Academy of Sciences

The title complex N,O-bis{2-[[(2,6-benzhydryl-4-methylphenyl)imino]-methyl]-phenol}-palladium(II)(C_(80)H_(64)N_2O_2 Pd) has been synthesized by the reaction of 2-[[(2,6-benzhydryl-4-methylphenyl)imino]-methyl]-phenol with Pd(CH_3COO)_2, and characterized by IR spectrum and elemental analysis. The spatial structure of the complex has been verified by single-crystal X-ray diffraction analysis. The compound belongs to the monoclinic system, space group P21/n with a = 13.492(3), b = 16.924(3), c = 14.135(3) ?, β = 97.84(3)°, V = 3197.4(11) ?~3, C_(80)H_(64)N_2O_2 Pd, Mr = 1191.73, Z = 2, Dc = 1.238 Mg/m^3, μ = 0.339 mm^(-1), F(000) = 1240, T = 293(2) K, the final R = 0.0593 and wR = 0.1192(I > 2s(I)). The compound showed excellent catalytic activity up to 1.130 × 10~7 g of PNB(mol of Pd)^(-1)h^(-1) for the addition polymerization of Norbornene by using methylaluminoxane(MAO) as a cocatalyst.

关键词： palladium complex Schiff-base crystal structure catalysis Norbornene polymerization

VINYL POLYMERIZATION OF Norbornene CATALYZED BY [2-(2-BENZIMIDAZOLYL)-6-((1-ARYLIMINOETHYL)PYRIDYL)]NICKEL CHLORIDE/MAO SYSTEM

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Chinese Journal of Polymer Science 2008年第5期26卷 561-565页

作者：左伟伟 Department of Materials Science and Engineering Beijing Institute of Petrochemical Technology

The catalytic system of[2-(2-benzimidazolyl)-6-((1-aryliminoethyl)pyridyl)]nickel chloride/MAO(methylalu- minoxane)was found to be good active for vinyl polymerization of Norbornene and provided polymers with relative narrow molecular distributions.Various reaction parameters,such as the ratios of nickel precursor to MAO or monomer Norbornene, and the nature of the ligands in complexes were carefully investigated to realize their effects on the catalytic activities, polymer molecular weight and molecular we...

关键词： Nickel complex 2-（2-Benzimidazolyl）-6-（1-aryliminoethyl）pyridyl Norbornene Vinyl polymerization of norbomene.

SYNTHESIS AND CHARACTERIZATION OF BIS-[2-[[(2-ALKOXYPHENYL)IMINO]METHYL]-PHENOLATO-O,N,O]NICKEL(II)COMPLEXES AND THEIR Norbornene POLYMERIZATION

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Chinese Journal of Polymer Science 2005年第6期23卷 619-626页

作者： Dong-heng Zhang Su-yun Jie Hai-jian Yang Fei Chang and Wen-hua Sun Key Laboratory of Engineering Plastics,Institute of Chemistry,Chinese Academy of Sciences,Beijing 100080,China Key Laboratory of Engineering Plastics Institute of Chemistry Chinese Academy of Sciences Beijing 100080 China

A series of salicylaldimines, synthesized in high yield via microwave-assisted condensation of salicylaldehyde and 2-alkoxyaniline were allowed to react with nickel chloride to form six-coordinated nickel complexes. These nickel complexes were carefully characterized, and the solid structure of la was elucidated by X-Ray diffraction. Activated with MAO, the nickel complexes showed good activity for homopolymerization of Norbornene. Reaction parameters, such as the ratio of nickel precursor to MAO, monomer concentration, reaction time and the reaction temperature, as well as the nature of the ligands were found to have significant effects on the catalytic activity and some properties of the resulting polyNorbornene.

关键词： Salicylaldirnine Nickel complex Norbornene Vinyl polymerization

High Norbornene incorporation in ethylene-Norbornene copolymerization with a bis(α-alkyloxoimine) titanium-MAO catalyst

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Science China Chemistry 2010年第8期53卷 1634-1640页

作者： GAO HaiYang1,2,HU Hao1 & WU Qing1,2 1Institute of Polymer Science,School of Chemistry and Chemical Engineering,Sun Yat-Sen (Zhongshan) University,Guangzhou 510275,China 2Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education Sun Yat-Sen (Zhongshan) University,Guangzhou 510275,China Institute of Polymer Science School of Chemistry and Chemical Engineering Sun Yat-Sen (Zhongshan) University Guangzhou China Key Laboratory for Polymeric Composite and Functional Materials of Ministry of Education Sun Yat-Sen (Zhongshan) University Guangzhou China

A novel bis(α-alkyloxoimine) titanium(IV) complex was synthesized and used as a catalyst precursor to catalyze homo-and copolymerization of ethylene and Norbornene.The titanium complex activated with methylalumoxane exhibits good activities for the homopolymerizations of ethylene and Norbornene under high temperature to produce high-molecular-weight linear polyethylene and vinyl-type polyNorbornene,respectively.Ethylene-Norbornene copolymers with high molecular weight can also be produced by this catalyst.The incorporation of Norbornene from 0 to 76 mol% in the copolymers can be controlled by varying the charged Norbornene.13C NMR analyses show that the microstructures of the ethylene-Norbornene copolymers with low Norbornene incorporation are predominantly alternated and isolated Norbornene units,while those with high Norbornene incorporation are random polymers containing long Norbornene sequences.

关键词： catalyst ethylene Norbornene polymerization copolymerization

Asymmetric Two-Component Alkenyl Catellani Reaction for the Construction of C-N Axial Chirality

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CHINESE JOURNAL OF CHEMISTRY 2024年第7期42卷 699-704页

作者： Wu, Chenggui Liu, Ze-Shui Shang, Yong Liu, Chang Deng, Shuang Cheng, Hong-Gang Cong, Hengjiang Jiao, Yinchun Zhou, Qianghui Wuhan Univ Inst Adv Studies Coll Chem & Mol Sci Sauvage Ctr Mol SciEngn Res Ctr Organosilicon Cpd Wuhan 430072 Hubei Peoples R China Wuhan Univ TaiKang Ctr Life & Med Sci Wuhan 430072 Hubei Peoples R China Anhui Univ Chinese Med Key Lab Xinan Med Minist Educ Hefei 230038 Anhui Peoples R China Hunan Univ Sci & Technol Sch Chem & Chem Engn Xiangtan 411201 Hunan Peoples R China

Herein, we report an asymmetric two-component alkenyl Catellani reaction for the construction of C-N axial chirality through a palladium/chiral Norbornene cooperative catalysis and an axial-to-axial chirality transfer process. Various partially aromatic iodinated 2-pyridones, quinolones, coumarin and uracil substrates react with 2,6-disubstituted aryl bromides with a tethered amide group, to afford a wide variety of polycyclic C-N atropisomers (38 examples, up to 97% e.e.). The obtained C-N axial chirality originates from the preformed transient C-C axial chirality with high fidelity. The synthetic utility of this chemistry is demonstrated by facile preparation of complex quinoline and pyridine based C-N atropisomers through a N-deprotection and aromatization sequence. In addition, a remote axial-to-central diastereoinduction process dictated by C-N axial chirality is observed with excellent diastereocontrol.

关键词： Alkenyl Catellani reaction Asymmetric catalysis Atropisomerism Axial-to-axial chirality transfer Heterocycles H FUNCTIONALIZATION AROMATIC FUNCTIONALIZATION ENANTIOSELECTIVE SYNTHESIS REGIOSELECTIVE SYNTHESIS STEREOCHEMICAL RELAY ARYL IODIDES PALLADIUM Norbornene PD/Norbornene ANNULATION

RING OPENING METATHESIS POLYMERIZATION OF Norbornene CATALYZED BY MCl4·2L/CH3Li

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Chinese Journal of Catalysis 1999年第5期20卷 489-490页

作者： Huang Jiling, Keleypette Dono, Ma Haiyan, Qian Yanlong (Laboratory of Organometallic Chemistry, East China University of Science and Technology, Shanghai 200237) 华东理工大学上海 200237

The ring opening metathesis polymerization of cyclic monomers is relatively a newcomer to the field of polymer chemistry. Depending on the monomer and the catalyst used, this type of reaction yields a wide range of pr... 详细信息

关键词： ywords ring opening metathesis polymerization Norbornene metal halide adduct complex nitrogen containing ligand oxygen containing ligand