Bin Liu

Zhejiang University, Hang-hsien, Zhejiang Sheng, China

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Publications (12)36.92 Total impact

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    ABSTRACT: A family of 2,9-di(3-R-1H-imidazolium-1-yl)-1,10-phenanthroline iodides and hexafluorophosphates (R = allyl, benzyl, mesityl, picolyl) were synthesized from 2,9-diiodophenanthroline and imidazole or N-substituted imidazoles. Simple reactions of these diimidazolium salts with copper powder at room temperature have afforded a series of multinuclear copper(I)-NHC complexes in good yields. The structures vary depending on the N substituents and counterions. [Cu4(L1)2(MeCN)4](PF6)4 (R = allyl) exhibits a zigzag Cu4 chain with two terminal [Cu(NHC)(MeCN)2] and two internal [Cu(phen)(NHC)] moieties. [Cu3(L2)2](PF6)3 (R = benzyl) contains a strictly linear Cu3 framework with two [Cu(NHC)2] units and a [Cu(phen)2] located at the center. Both complexes [Cu3(L4)2](PF6)3 (R = mesityl) and [Cu3(L5)2](PF6)3 (R = picolyl) consist of a triangular Cu3 core in which two copper(I) ions are surrounded by a phen and a NHC group and the third copper(I) is coordinated by two NHC groups. [Cu3(L3)2](PF6)3 derived from 2,9-di(3-benzyl-1H-benzimidazolium-1-yl)-1,10-phenanthroline hexafluorophosphate can undergo transannulation of the benzimidazolylidene ring giving [Cu2(L3')2](PF6)2. The decomposition process might involve solvent-induced rearrangement of the ligand and hydrolysis of carbene moieties. Treatment of 2,9-di(3-mesityl-1H-benzimidazolium-1-yl)-1,10-phenanthroline iodide with copper powder generated dinuclear complex [Cu2(L4)2][Cu2(μ-I)2I2] (R = mesityl) possessing a macrocyclic cation and [Cu2(μ-I)2I2](2-) anion. Tetranuclear complex [Cu4(L5)2(μ-I)2](CuI3) (R = picolyl) has been obtained from its diimidazolium iodide and copper powder. All Cu(I) complexes have been characterized by X-ray single diffraction analysis, elemental analysis, and NMR spectra. Their redox behavior and fluorescent properties have also been studied.
    Inorganic chemistry. 09/2014;
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    ABSTRACT: Reactions of [FeL2(CH3CN)2]2+ (L = N-pyrimid-2-ylimidazolylidene) with various N-, P-, O-, and S-donors were investigated. By replacing the labile acetonitrile, various iron-NHC complexes containing additional N-, P-, O-, and S-ligands were prepared. All the iron-NHC complexes were fully characterized by NMR spectroscopy and X-ray crystallography. [FeL2(CH3CN)2]2+ could efficiently catalyze the coupling reactions of various Grignard reagents with heteroaryl bromides or chlorides.
    Chinese Science Bulletin 07/2012; 57(19). · 1.37 Impact Factor
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    ABSTRACT: A novel electrochemical procedure for the preparation of metal complexes of N-heterocyclic carbenes using imidazolium salts or corresponding silver-NHC complexes as carbene sources and electrolytes, and metal plates as the sacrificial anodes is described. The procedure is simple and good yielding without the use of expensive or air-sensitive reagents.
    Chemical Communications 03/2011; 47(10):2883-5. · 6.38 Impact Factor
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    ABSTRACT: Reactions of the imidazolium salts or their corresponding silver carbene complexes with copper powder afforded unusual copper(II) hydroxide complexes of N-heterocyclic carbenes: [Cu2(μ-OH)(L1)](PF6)2 (2; L1 = 3,5-bis(N-picolylimidazolylidenylmethyl)pyrazolate), [Cu4(μ3-OH)2(L2)2](PF6)4 (3; L2 = 3,5-bis(N-pyridylimidazolylidenylmethyl)pyrazolate), and [Cu4(μ3-OH)2(L3)2](PF6)4 (4; L3 = 3,5-bis(N-pyrimidylimidazolylidenylmethyl)pyrazolate). The same reaction of 3,5-bis(N-thiophenylimidazoliumylmethyl)pyrazole yielded a dinuclear Cu(II)−NHC complex, [Cu2(L4)2](PF6)2 (5; L4 = 3,5-bis(N-thiophenylimidazolylidenylmethyl)pyrazolate). The complexes have been fully characterized by X-ray diffraction analysis, elemental analysis, and IR and ESI-MS spectra. A catalytic study shows that complex 4 is highly active in the N-arylation reactions of imidazoles and aromatic amines with arylboronic acids in methanol at room temperature under base-free conditions.
    Organometallics 02/2010; 29(6). · 4.15 Impact Factor
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    ABSTRACT: Cobalt(iii) complexes, [CoCl(2)(L1)(2)](PF(6)) (1, L1 = N-methyl-N-(2-pyrimidinyl)imidazolylidene), [CoCl(L2)(2)](PF(6))(2) (, L2 = N-picolyl-(2-pyrimidinyl)imidazolylidene), [Co(L3)(2)](PF(6))(3) (3, L3 = bis(N-2-pyrimidylimidazolylidenyl)methane) and [CoCl(2)(L3)](PF(6)) (4) have been prepared from the corresponding pyrimidine functionalized imidazolium salts [HL1](PF(6)), [HL2](PF(6)), and [H(2)L3](PF(6))(2)via in situ generated silver carbene complexes under mild conditions. These cobalt complexes were characterized by (1)H and (13)C NMR spectroscopy and X-ray diffraction analysis. The cobalt complexes have been found to be good catalyst precursors for Kumada-Corriu cross-coupling reactions of aryl halides and Grignard reagents at room temperature. Complex 1 is more active under the mild conditions.
    Dalton Transactions 09/2009; · 4.10 Impact Factor
  • Angewandte Chemie International Edition 07/2009; 48(30):5513-6. · 11.34 Impact Factor
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    ABSTRACT: A family of tetra-, penta-, and hexacoordinate nickel complexes of functionalized N-heterocyclic carbene (NHC) ligands have been prepared via carbene transfer reactions of Ni(PPh3)2Cl2 and silver-NHC complexes in situ generated from corresponding imidazolium salts and Ag2O. These nickel(II) complexes have been characterized by 1H NMR, 13CNMR, and ESI spectroscopy and X-ray diffraction analysis. Structural analysis revealed that [Ni(L1)3](PF6)2 (L1 = 3-butyl-1-(5,7-dimethyl-1,8-naphthyridin-2-yl)imidazolylidene, 3) is a rare example of a nickel complex with trigonal-bipyramidal geometry. [Ni(L4)2](PF6)2 (L4 = 1-butyl-3-((7-methyl-1,8-naphthyridin-2-yl)methyl)imidazolylidene, 5) and [Ni(L20)2](PF6)2 (L20 = 3-(pyridin-2-ylmethyl)-1-(pyrimidin-2-yl)imidazolylidene, 21) are normal square-planar. [Ni(L8)3](PF6)2 (L8 = 3-methyl-1-(pyrimidin-2-yl)imidazolylidene, 9), [Ni(L10)2(CH3CN)](PF6)2 (L10 = 3-ethyl-1-(pyrimidin-2-yl)imidazol-ylidene, 11), [Ni(L12)2(CH3CN)](PF6)2 (L12 = 3-butyl-1-(pyrimidin-2-yl)imidazolylidene, 13), [Ni(L14)2(CH3CN)](PF6)2 (L14 = 3-benzyl-1-(pyrimidin-2-yl)imidazolylidene, 15), and [Ni(L16)2(CH3CN)](PF6)2 (L16 = 3-isopropyl-1-(pyrimidin-2-yl)imidazolylidene, 17) are pentacoordinate, displaying unusual square-pyramidal geometry. [Ni(L12)3](PF6)2 (L9 = 3-butyl-1-(pyrimidin-2-yl)imidazolylid-ene, 19), [Ni(L22)2(CH3CN)2](PF6)2 (L22 = 3-(2,6-diisopropylphenyl)-1-(pyrimidin-2-yl)imidazolylidene, 23), and [Ni(L24)(CH3CN)(H2O)] (L22 = 3-(2,4,6-trimethylphenyl)-1-(pyrimidin-2-yl)imidazolylidene, 25) are octahedral complexes. The structural diversity of these nickel(II) complexes originating from steric pressure of the ligands is discussed.
    Organometallics. 03/2009; 28(5).
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    ABSTRACT: The Kumada cross-coupling reaction of a variety of unactivated aryl chlorides, vinyl chlorides, and heteroaryl chlorides catalyzed by nickel(II) complexes containing pyridine-functionalized NHC ligands is described. The catalysts are so active that the reactions proceed at room temperature in excellent yields.
    The Journal of Organic Chemistry 06/2008; 73(10):3954-7. · 4.56 Impact Factor
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 01/2008; 39(17).
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    ABSTRACT: ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 200 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
    ChemInform 01/2008; 39(38).
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    ABSTRACT: The imidazolium salts bis(N-(pyridylmethyl)imidazoliumyl)methane hexafluorophosphate (H2L1·(PF6)2), 2,2‘-bis(N-(pyridylmethyl)imidazoliumyl)ethyl ether (H2L2·(PF6)2), 2,6-bis(N-(pyridylmethyl)imidazoliumyl)pyridine (H2L3·(PF6)2), and 3,6-bis(N-(pyridylmethyl)imidazoliumyl)pyridazine (H2L4·(PF6)2) have been prepared and characterized. They reacted with Ag2O in acetonitrile to produce the silver complexes [Ag4(L1)2(CH3CN)2](PF6)4·2CH3CN (1), [Ag4(L2)2](PF6)4·2CH3CN (2), [Ag4(L3)2](PF6)4·Et2O·CH3CN (4), and [Ag6(L4)4](PF6)6 (5), respectively. The reaction of 2 with 4 equiv of Au(Et2S)Cl afforded the dimetallic gold complex [Au2(L2)](PF6)2·2CH3CN (3). Complexes 1−4 were characterized by 1H NMR, 13C NMR, luminescence spectroscopy, elemental analyses, and X-ray crystallography. Complex 1 is a tetrasilver complex consisting of a zigzag silver chain with silver−silver separations of 2.911(1) and 3.288(1) Å. Complexes 2 and 4 have orthogonal tetrasilver cores in which four silver atoms are held together by two L2 or L3 ligands with relatively short Ag−Ag contacts ranging from 2.790(1) to 3.293(2) Å. The digold complex consists of a macrometallocycle formed by two gold atoms and one L2 ligand, and the intramolecular Au−Au bond distance is 3.267(1) Å. Complex 5 is a hexamer with six silver atoms bridged by four L4 ligands forming three silver−silver bonds of distances 3.249(2), 3.014(2), and 3.089(2) Å. ESI-MS spectra show that these multinuclear silver cores are retained in acetonitrile solution. All of these silver complexes are intensely luminescent in their solid state.
    Organometallics 06/2007; 26(15). · 4.15 Impact Factor
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    ABSTRACT: An efficient route to synthesize the heteroaryl-substituted 1,8-naphthyridine derivatives was described. Eight 2-heteroaryl- and 2,7-diheteroaryl-1,8-naphthyridine derivatives were obtained through palladium-catalyzed C–N-coupling reactions of chloronaphthyridines with imidazole, benzimidazole, morpholine, 3,5-dimethylpyrazole, and phthalimide in moderate to good yields.
    Chinese Chemical Letters 01/2007; 18(4):383-386. · 1.18 Impact Factor