Hai-Bin Song

Nankai University, T’ien-ching-shih, Tianjin Shi, China

Are you Hai-Bin Song?

Claim your profile

Publications (217)470 Total impact


  • No preview · Article · Aug 2015 · Letters in Drug Design & Discovery
  • Da-Wei Zhao · Yi Xu · Yao-Wei Guo · Hai-Bin Song · Liang-Fu Tang
    [Show abstract] [Hide abstract]
    ABSTRACT: Treatment of 1-methyl-3,5-dialkylpyrazoles with n-BuLi, and subsequently with iron carbonyl and iodine yielded (pyrazol-1-yl)acyl iron complexes CH2(CO) (3,5-R2Pz)Fe(CO)3I (R = Me or Pri, Pz = pyrazol-1-yl). Reaction of CH2(CO) (3,5-Me2Pz)Fe(CO)3I with PhSNa gave a dimeric complex [CH2(CO) (3,5-Me2Pz)Fe(CO)2(SPh)]2, while similar reactions of CH2(CO) (3,5-R2Pz)Fe(CO)3I with PySNa (Py = 2-pyridyl) gave mononuclear complexes CH2(CO) (3,5-R2Pz)Fe(CO)2(SPy), which exhibited an isomerization in solution. Treatment of the dimeric complex with PPh3 at room temperature resulted in the decomposition of the starting material. Furthermore, this dimeric complex readily underwent reductive elimination to generate CH2(COSPh) (3,5-Me2Pz) when heated at relatively low temperature, and thermal decomposition reaction to give PhSSPh in refluxing toluene solution. Reaction of mononuclear complexes with PPh3 caused one carbonyl to be replaced by phosphine ligand to give complexes CH2(CO) (3,5-R2Pz)Fe(CO) (PPh3) (SPy). All these acyl iron complexes were fully characterized by IR and NMR spectroscopy, and their structures were unambiguously determined by X-ray crystallography.
    No preview · Article · Aug 2015 · Journal of Organometallic Chemistry
  • Cai-Hong Cheng · Ren-Yu Guo · Qi Cui · Hai-Bin Song · Liang-Fu Tang
    [Show abstract] [Hide abstract]
    ABSTRACT: A series of N-heterocyclic carbene transition metal (molybdenum, tungsten and ruthenium) carbonyl complexes derived from 1-[2-(pyrazol-1-yl)phenyl]-imidazole have been synthesized and characterized by physico-chemical and spectroscopic methods, and the structures of five complexes have been confirmed by X-ray crystal structure analyses. The azaaryl-functionalized N-heterocyclic carbenes act as chelating N,C-bidentate ligands in these five complexes. Preliminary catalytic tests of these NHC-molybdenum (tungsten) carbonyl complexes in the oxidation of styrene have been carried out, showing that benzaldehyde was the main oxidation product when hydrogen peroxide was used as the oxidant, while 2,5-diphenyl-1,4-dioxane was obtained as the exclusive product in the oxidation by tert-butyl hydroperoxide.
    No preview · Article · Apr 2015 · Transition Metal Chemistry
  • [Show abstract] [Hide abstract]
    ABSTRACT: In order to study the potential bioactivities of 4-amino tetramic acid derivatives, the 4-amination products of pyrrolidine-2,4-diones (5) and 4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylates (4) were prepared. The 4-amination of 5 took place in high yield when catalyzed by acetic acid, whereas the 4-amination of 4 was achieved through a 4-ethoxy intermediate, which was prepared by acidic etherification. Their herbicidal, fungicidal, insecticidal, and antitumor activities were tested. The bioassays showed that two of the compounds exhibited good herbicidal activity against dicot Arabidopsis thaliana at a concentration of 10 µg/mL, and one compound gave instinct fungicidal activity against Pythium sp. at a concentration of 2 µg/mL.
    No preview · Article · Mar 2015 · Journal of Heterocyclic Chemistry
  • [Show abstract] [Hide abstract]
    ABSTRACT: A series of novel N-phenylpyrazolyl aryl methanones derivatives containing the arylthio/sulfinyl/sulfonyl group have been synthesized via multi-step reactions from 3-methyl-1-phenyl-1H-pyrazol-5(4H)-one and characterized by melting point, 1H NMR, 13C NMR, FT-IR, and HRMS. The crystal structure of (5-(4-chlorophenylsulfonyl)-3-methyl-1-phenyl-1H-pyrazol-4-yl)(2,4-dichlorophenyl)methanone containing the arylsulfonyl moiety is reported. The biological activity results showed that some of the title compounds exhibit favorable herbicidal and insecticidal activities.
    No preview · Article · Jan 2015 · Phosphorus Sulfur and Silicon and the Related Elements
  • Fang-Lin Li · Qi Chen · Hai-Bin Song · Bin Dai · Liang-Fu Tang
    [Show abstract] [Hide abstract]
    ABSTRACT: Bis(pyrazol-1-yl)methane-tetracarboxylic acid and tris(pyrazol-1-yl)methane-hexacarboxylic acid, namely bis(3,5-dicarboxypyrazol-1-yl)methane (CH2[3,5-Pz(CO2H)2]2) and tris(3,5-dicarboxypyrazol-1-yl)methane (CH[3,5-Pz(CO2H)2]3), have been synthesized by the oxidation reaction of bis(3,5-dimethylpyrazol-1-yl)methane and tris(3,5-dimethylpyrazol-1-yl)methane with an excess of KMnO4. Reaction of CH2[3,5-Pz(CO2H)2]2 with (R3Sn)2O yielded the corresponding organotin polycarboxylates (CH2[3,5-Pz(CO2SnR3)2]2, R = Et (1) and n-Bu (2), respectively). The structures of these two complexes have been confirmed by X-ray structural analyses. Complex 1 formed a coordination polymer containing fused 22- and 24-membered macrocyclic units. While complex 2 created a double-layer macrocyclic structure by the bridging coordination of carboxylate groups to the tin atoms as well as the hydrogen bonds in coordinated waters. Reaction of CH[3,5-Pz(CO2H)2]3 with (Ph3Sn)2O yielded hexanuclear triphenyltin polycarboxylate CH[3,5-Pz(CO2SnPh3)2]3, which did not assemble into a supramolecular architecture like those in complex 1 or 2, possibly owing to the relatively large steric hindrance of the phenyl groups as well as the relatively large size of the hexabasic carboxylic acid.
    No preview · Article · Nov 2014 · Polyhedron
  • Jian-Peng Sun · Da-Wei Zhao · Hai-Bin Song · Liang-Fu Tang
    [Show abstract] [Hide abstract]
    ABSTRACT: (3,5-Dimethylpyrazol-1-yl)carbonyl- and n-butoxycarbonyl-functionalized bis(3,5-dimethylpyrazol-1-yl)methide carbonyl tungsten derivatives were unexpectedly formed, together with a bis(3,5-dimethylpyrazol-1-yl)acyl carbonyl tungsten complex, upon sequential treatment of bis(3,5-dimethylpyrazol-1-yl)methane with n-BuLi, tungsten carbonyl, and iodine. The resulting complexes were fully characterized using IR and NMR spectroscopy, and their structures were unambiguously determined by X-ray crystallography.
    No preview · Article · Sep 2014 · Organometallics
  • [Show abstract] [Hide abstract]
    ABSTRACT: As the active site models of [NiFe]-hydrogenases, a series of trinuclear complexes (diphosphine) Ni(mu(3)-E)(2)Fe-2(CO)(6) (1-10, diphosphine = dppv, dppb, dppf, dppe, (Ph2PCH2)(2)NR (R = Me, t-Bu; E = S, Se, Te) has been prepared by the one-pot reactions of (mu-E-2)Fe-2(CO)(6) with Et3BHLi, followed by treatment of the resultant intermediates (mu-LiE)(2)Fe-2(CO)(6) with the corresponding mononuclear complexes (diphosphine) NiCl2. All the new complexes 1-10 have been fully characterized by elemental analysis, spectroscopy, and X-ray crystallography. Electrochemical study reveals that reductions of the three representative complexes (dppv) Ni(mu(3)-E)(2)Fe-2(CO)(6) (1, E = S; 3, Se; 8, Te) become easier from the S to Se to Te complexes. Furthermore, electrocatalytic study demonstrates that complexes 1, 3, and 8 are catalysts for proton reduction to hydrogen in the presence of proton source HOTs.
    No preview · Article · Jul 2014 · Journal of Organometallic Chemistry
  • Hai-Jun Li · Xia-Li Liu · Ke Ding · Hai-Bin Song · Liang-Fu Tang
    [Show abstract] [Hide abstract]
    ABSTRACT: Bis(1-methylimidazol-2-yl)methane and 1-(1-methylimidazol-2-yl)methyl-3,5-dimethylpyrazole[CH2(min)(pz)] could be deprotonated with n-BuLi at the bridging carbon atom. The corresponding anions were inactive in the reaction with Ph3SnCl but reacted with sulfur, followed by reaction with Ph2SnCl2 to give organotin derivatives Ph2ClSnSCH(min)(2) (1) and Ph2ClSnSCH(min)(pz) (4) (min = 1-methylimidazol-2-yl and pz = 3,5-dimethylpyrazol-1-yl, respectively). The structure of 1 determined by X-ray structural analyses indicated that bis(1-methylimidazol-2-yl)methylthiolate acted as a bidentate monoanionic kappa(2)-[N,S] chelating ligand. Reaction of 1 with W(CO)(5)THF yielded heterobimetallic complex Ph2ClSnSCH(min)(2)W(CO)(5) (2), while similar reaction of 4 with W(CO)(5)THF resulted in the decomposition of 4 to give pyrazole derivative W(CO)(5)(pzH). The structure of 2 has been confirmed by X-ray structural analyses, showing that 1 coordinated to the tungsten atom through the free nitrogen atom. Reaction of CH2(min)(pz) with W(CO)(5)THF yielded bidentate chelating complex CH2(min)(pz)W(CO)(4), which when treated with n-BuLi, followed by reaction with Ph3SnCl, gave the final product CH2(minSnPh(3))(pz) W(CO)(4).
    No preview · Article · May 2014 · Journal of Organometallic Chemistry
  • [Show abstract] [Hide abstract]
    ABSTRACT: As biomimetic models for [Fe]-hydrogenase, the 2-acylmethyl-6-ester group-difunctionalized pyridine-containing iron(ii) complexes have been successfully prepared via the following three separate steps. In the first step, the acylation or esterification of difunctionalized pyridine 2-(p-MeC6H4SO3CH2)-6-HOCH2C5H3N with acetyl chloride or benzoic acid gives the corresponding pyridine derivatives 2-(p-MeC6H4SO3CH2)-6-RCO2CH2C5H3N (, R = Me; , R = Ph). The second step involves reaction of or with Na2Fe(CO)4 followed by treatment of the intermediate Fe(0) complexes [Na(2-CH2-6-RCO2CH2C5H3N)Fe(CO)4] (, R = Me; , R = Ph) with iodine to afford 2-acylmethyl-6-acetoxymethyl or 6-benzoyloxymethyl-difunctionalized pyridine-containing Fe(ii) iodide complexes [2-C(O)CH2-6-RCO2CH2C5H3N]Fe(CO)2I (, R = Me; , R = Ph). Finally, when or is treated with sodium 2-mercaptopyridinate, the corresponding difunctionalized pyridine-containing Fe(ii) mercaptopyridinate complexes [2-C(O)CH2-6-RCO2C5H3N]Fe(CO)2(2-SC5H4N) (, R = Me; , R = Ph) are produced. While the structures of model complexes are confirmed by X-ray crystallography, the electrochemical properties of and are compared with those of the two previously reported models. In addition, complexes and have been found to be catalysts for H2 production in the presence of TFA under CV conditions.
    No preview · Article · Apr 2014 · Dalton Transactions
  • [Show abstract] [Hide abstract]
    ABSTRACT: Diiron carbonyl complex [{(μ-SCH2)2O}Fe2(CO)6] (A) reacted with Ph2PCl and Me3NO in MeCN at room temperature to give the expected and unexpected Ph2PCl-, Ph2PNMe2-, and Ph2PP(=O)Ph2-substituted complexes [{(μ-SCH2)2O}Fe2(CO)5L] [1, L = Ph2PCl; 2, L = Ph2PNMe2; 3, L = Ph2PP(=O)Ph2], whereas complex [{(μ-SCH2)2CH2}Fe2(CO)6] (B) reacted with Ph2PCl and Me3NO under similar conditions to afford only the unexpected complexes [{(μ-SCH2)2CH2}Fe2(CO)5L] [4, L = Ph2PNMe2; 5, L = Ph2PP(=O)Ph2]. Similarly, complex [{(μ-SeCH2)2O}Fe2(CO)6] (C) reacted with Ph2PCl and Me3NO in MeCN at room temperature to give the unexpected complexes [{(μ-SeCH2)2O}Fe2(CO)5L] [6, L = Ph2PNMe2; 7, L = Ph2PP(=O)Ph2], and the corresponding unexpected complexes [{(μ-SeCH2)2CH2}Fe2(CO)5L] [8, L = Ph2PNMe2; 9, L = Ph2PP(=O)Ph2] were produced by the reaction of complex [{(μ-SeCH2)2CH2}Fe2(CO)6] (D) with Ph2PCl and Me3NO under similar conditions. The structures of 1–9 were characterized by elemental analysis and spectroscopy, and for 1–5 and 7–9 by X-ray crystallography. Possible pathways for the formation of the functionalized phosphine-substituted complexes 1–9 have been suggested. Complexes 1–9 can be regarded as models for [FeFe] hydrogenases as their structures are similar to the active site of [FeFe] hydrogenases, and some have been found to be catalysts for proton reduction to hydrogen in the presence of HOAc.
    No preview · Article · Apr 2014 · Berichte der deutschen chemischen Gesellschaft
  • [Show abstract] [Hide abstract]
    ABSTRACT: Based on structures of insecticidal chlorfenapyr and antibiotic natural pyrrolomycins, a series of new 2-benzylpyrroles and 2-benzoylpyrroles (with or without ethoxymethyl group on the nitrogen of pyrrole) were designed and synthesized. These compounds or their parent compounds possess weak acidity and high lipophilicity, the two characteristic properties for uncouplers of oxidative phosphorylation; therefore, they are expected to have insecticidal and acaricidal activity. The bioassay result verified that both 2-benzylpyrroles 17 and 2-benzoylpyrroles 19 had varied degrees of insecticidal activity against oriental armyworm depending on the substituents on the benzene ring, but they did not give any acaricidal activity. Conversely, most N-alkylated compounds 18 and 20 exhibited both insecticidal activity and acaricidal activity, of which compound 18i [4-bromo-2-(2,4-dichlorobenzyl)-1-(ethoxymethyl) -5-(trifluoromethyl) - 1[Formula: see text]-pyrrole-3-carbonitrile] has IC[Formula: see text] as low as 10-20 mg L[Formula: see text] on both activities.
    No preview · Article · Mar 2014 · Molecular Diversity
  • [Show abstract] [Hide abstract]
    ABSTRACT: In order to study the potential bioactivities of 4-amino tetramic acid derivatives, the 4-amination products of pyrrolidine-2,4-diones (5) and 4-hydroxy-2-oxo-2,5-dihydro-1H-pyrrole-3-carboxylates (4) were prepared. The 4-amination of 5 took place in high yield when catalyzed by acetic acid, whereas the 4-amination of 4 was achieved through a 4-ethoxy intermediate, which was prepared by acidic etherification. Their herbicidal, fungicidal, insecticidal, and antitumor activities were tested. The bioassays showed that two of the compounds exhibited good herbicidal activity against dicot Arabidopsis thaliana at a concentration of 10 µg/mL, and one compound gave instinct fungicidal activity against Pythium sp. at a concentration of 2 µg/mL.
    No preview · Article · Mar 2014 · Journal of Heterocyclic Chemistry
  • Cai-Hong Cheng · Jia-Ru Xu · Hai-Bin Song · Liang-Fu Tang
    [Show abstract] [Hide abstract]
    ABSTRACT: Three pyrazolyl-functionalized N-heterocyclic carbene (NHC) palladium complexes based on 1-[2-(pyrazol-1-yl)phenyl]imidazole have been synthesized and characterized by physico-chemical and spectroscopic methods, and the structures of two of the complexes have been confirmed by single-crystal X-ray diffraction. The pyrazolyl-functionalized NHCs act as chelating N,C-bidentate ligands in these three complexes. Catalytic tests have proved that these complexes exhibit highly effective catalytic activity for the Suzuki–Miyaura and Mizoroki–Heck coupling reactions in water or aqueous/organic media under air. The substituents on the pyrazolyl ring exert different influences on the catalytic activity of the complexes in these coupling reactions.
    No preview · Article · Mar 2014 · Transition Metal Chemistry
  • [Show abstract] [Hide abstract]
    ABSTRACT: With H2 O or NH3 stimuli, blue cobalt-based metal-organic framework (MOF) BP can reversibly transform to red RP. The removal/recovery of terephthalate ligands accompanied by the transformation leads to a gate effect, which allows the encapsulation and release of small solvent molecules under certain conditions. This is the first example of topology transformation from a self-penetrating to interpenetrating net in 3D MOFs.
    No preview · Article · Oct 2013 · Angewandte Chemie International Edition
  • Li-Cheng Song · Ling Li · Yuan-Yuan Hu · Hai-Bin Song
    [Show abstract] [Hide abstract]
    ABSTRACT: A new series of (diphosphine)Ni-bridged double-butterfly Fe/S clusters [(μ-RS)( μ-S]CS)Fe2(CO)6]2[Ni(- diphosphine)] (1-6, R = p-MeC6H4, Ph, n-Bu; diphosphine = dppe, dppv, dppb, dppf) was prepared by a new type of sequential reactions of the m-CO-containing anions [(μ-RS)( μ-CO)Fe2(CO) 6]- (type A anions, generated in situ from Fe 3(CO)12, RSH, and Et3N) with excess CS 2, followed by treatment of the resulting m-CS2-containing anions [(μ-RS)( μ-S]CS)Fe2(CO)6]- (type B anions) with various (diphosphine)NiCl2 complexes. In addition, two of the type A anions, namely [(μ-p-MeC6H4S)( μ-CO)Fe2(CO)6]- (A1) and [(μ- PhS)( μ-CO)Fe2(CO)6]- (A2) were successfully isolated as their [Et3NH] and [Ph4P] salts, respectively. Products 1-6 as well as the two isolated complex salts A1[Et 3NH] and A1[Ph4P] were fully characterized by elemental analysis and spectroscopy, and particularly for 4, 6, A 1[Et3NH], and A2[Ph4P] by X-ray crystallography.
    No preview · Article · Oct 2013 · Journal of Organometallic Chemistry
  • Li-Cheng Song · Jia-Peng Li · Zhao-Jun Xie · Hai-Bin Song
    [Show abstract] [Hide abstract]
    ABSTRACT: Four new dinuclear Ni/Mn model complexes RN(PPh2)2Ni(μ-SEt)2(μ-Cl)Mn(CO)3 (7, R = p-MeC6H4CH2; 8, R = EtO2CCH2) and RN(PPh2)2Ni(μ-SEt)2(μ-Br)Mn(CO)3 (9, R = p-MeC6H4CH2; 10, R = EtO2CCH2) have been prepared via the four separated step-reactions involving six new precursors RN(PPh2)2 (1, R = p-MeC6H4CH2; 2, R = EtO2CCH2), RN(PPh2)2NiCl2 (3, R = p-MeC6H4CH2; 4, R = EtO2CCH2), and RN(PPh2)2Ni(SEt)2 (5, R = p-MeC6H4CH2; 6, R = EtO2CCH2). The Et3N-assisted aminolysis of Ph2PCl with p-MeC6H4CH2NH2 or EtO2CCH2NH2·HCl in CH2Cl2 gave the azadiphosphine ligands 1 and 2 in 38% and 53% yields, whereas the coordination reaction of 1 or 2 with NiCl2·6H2O in CH2Cl2/MeOH afforded the mononuclear Ni dichloride complexes 3 and 4 in 59% and 78% yields, respectively. While thiolysis of 3 or 4 with EtSH under the assistance of Et3N in CH2Cl2 produced the mononuclear Ni dithiolate complexes 5 and 6 in 64% and 68% yields, further treatment of 5 and 6 with Mn(CO)5Cl or Mn(CO)5Br resulted in formation of the dinuclear Ni/Mn model complexes 7-10 in 31-73% yields. All the new compounds 1-10 have been structurally characterized, while model complexes 7 and 9 have been found to be catalysts for HOAc proton reduction to hydrogen under CV conditions.
    No preview · Article · Sep 2013 · Inorganic Chemistry
  • [Show abstract] [Hide abstract]
    ABSTRACT: Based on the structures of the 4-hydroxyphenylpyruvate dioxygenase inhibitor mesotrione and natural product fischerellin A, a series of imine derivatives of ([Formula: see text])-3-acyl-quinoline-2,4(1H,3H)-dione (6, 12 and 16) were designed, synthesized and systematically evaluated for their herbicidal activity. The bioassay results indicated that most of the synthesized compounds displayed good to excellent herbicidal activity, of which 6e, 6g, 6h, 6q and 6t exhibited more than 50 % inhibition against Brassica napus L., Amaranthus retroflexu or Digitaria adscendens at a dosage of [Formula: see text] or lower. The symptom of injured leaves in vivo, the high Hill reaction inhibitory activity of 6h in vitro ([Formula: see text] and the computer-based binding model of compound 6h with D1 protein in photosystem II (PSII) reaction centre suggest this novel structure to likely be a new type of PSII electron transport inhibitor. Thus, we have found a novel type of diketone enamine structure targeted at the PSII reaction centre.
    No preview · Article · Aug 2013 · Molecular Diversity
  • Chen Chen · Yi-Zhou Zhu · Qiao-Jun Fan · Hai-Bin Song · Jian-Yu Zheng
    [Show abstract] [Hide abstract]
    ABSTRACT: Supramolecular interactions of cobalt corrole and fullerene were investigated both in solution and the solid state. Results reveal that cobalt corrole has the attractive ability to be used as host for fullerene. The cocrystals of cobalt corrole and C-60/C-70 suitable for X-ray crystallographic analysis were obtained and structure details are discussed.
    No preview · Article · Aug 2013 · Tetrahedron Letters
  • Qiang Li · Xin Li · Jun Yang · Hai-Bin Song · Liang-Fu Tang
    [Show abstract] [Hide abstract]
    ABSTRACT: A series of N-heterocyclic carbene (NHC) silver complexes derived from N-ferrocenylmethyl-N'-(pyridylmethyl)imidazolium iodides have been synthesized, which show remarkable structural diversity. Reaction of N-ferrocenylmethyl-N'-(2-pyridylmethyl)imidazolium iodide with Ag2O yielded stair-like NHC-Ag complexes, whose assembly modes significantly depended on experimental conditions. Reaction of N-ferrocenylmethyl-N'-(4-pyridylmethyl)imidazolium iodide with Ag2O yielded a chain NHC-Ag complex with a repeating 16-membered macrocyclic unit. However, similar reaction of N-ferrocenylmethyl-N'-(3-pyridylmethyl)imidazolium iodide with Ag2O only gave a dimeric NHC-Ag complex through bridging iodide. In these NHC-Ag complexes, 2- and 4-pyridyl-substituted NHCs act as bridging bidentate ligands through the pyridyl nitrogen and carbene carbon atoms, while 3-pyridyl-substituted NHC only acts as a monodentate ligand through the carbene carbon atom. An I/CI exchange reaction was observed upon recrystallization of these NHC silver iodides in CH2Cl2. These NHC-Ag complexes exhibited highly effective catalytic activity in the three-component coupling reaction of alkyne, aldehyde and amine to generate propargylamines.
    No preview · Article · Aug 2013 · Polyhedron

Publication Stats

3k Citations
470.00 Total Impact Points

Institutions

  • 2003-2015
    • Nankai University
      • • State Key Laboratory of Elemento-Organic Chemistry
      • • Department of Chemistry
      T’ien-ching-shih, Tianjin Shi, China
  • 2007
    • Anhui Normal University
      Wu-hu-shih, Anhui Sheng, China
  • 2000-2004
    • The Chinese University of Hong Kong
      • Department of Chemistry
      Hong Kong, Hong Kong