Co-reporter:Xiaoning Song, Cong Xu, Dongxu Du, Ziming Zhao, Dongsheng Zhu, and Mang Wang
Organic Letters December 15, 2017 Volume 19(Issue 24) pp:6542-6542
Publication Date(Web):December 5, 2017
DOI:10.1021/acs.orglett.7b03254
A silver-catalyzed, defluorination ring-opening diarylation of siloxy 2,2-difluorocyclopropanes, with two arenes, to directly prepare polysubstituted 2-fluoroallylic compounds, is described. This multicomponent reaction proceeds smoothly in good stereoselectivity, which is due to a chelation-controlled addition of arenes to α-fluorinated ketone intermediate.
Co-reporter:Jian Chang, Cong Xu, Jie Gao, Fengyun Gao, Dongsheng Zhu, and Mang Wang
Organic Letters April 7, 2017 Volume 19(Issue 7) pp:
Publication Date(Web):March 23, 2017
DOI:10.1021/acs.orglett.7b00611
A complete self-assistance strategy based on Me3SiCF2Br was used in the domino conversion of methylvinylketones into α,α-difluorinated cyclopentanones. Initiated by 5 mol % of nBu4NBr, the multistep reaction occurred in one pot under mild conditions via the in situ formation of silyl dienol ethers, difluorocyclopropanation, thermal vinylcyclopropane–cyclopentene rearrangement, and desilylation. The process takes advantage of the multitasking capability of Me3SiCF2Br as the difluorocarbene source, a silicon-based transfer agent, and a bromine anion releaser.
Co-reporter:Jingwen Liang, Mehboob Hassan, Dongsheng Zhu, Liping Guo, Xiangjie Bo
Journal of Colloid and Interface Science 2017 Volume 490(Volume 490) pp:
Publication Date(Web):15 March 2017
DOI:10.1016/j.jcis.2016.11.101
Nitrogen-doped graphene (N/GR) has been considered as active metal-free electrocatalysts for oxygen reduction reaction (ORR). However, the nitrogen (N) doping efficiency is very low and only few N atoms are doped into the framework of GR. To boost the N doping efficiency, in this work, a confined pyrolysis method with high N doping efficiency is used for the preparation of cobalt nanoparticles/nitrogen-doped GR (Co/N/GR). Under the protection of SiO2, the inorganic ligand NH3 in cobalt amine complex ([Co(NH3)6]3+) is trapped in the confined space and then can be effectively doped into the framework of GR without the introduction of any carbon residues. Meanwhile, due to the redox reaction between the cobalt ions and carbon atoms of GR, Co nanoparticles are supported into the framework of N/GR. Due to prevention of GR layer aggregation with SiO2, the Co/N/GR with high dispersion provides sufficient surface area and maximum opportunity for the exposure of Co nanoparticles and active sites of N dopant. By combination of enhanced N doping efficiency, Co nanoparticles and high dispersion of GR sheets, the Co/N/GR is remarkably active, cheap and selective noble-metal free catalysts for ORR.Download high-res image (170KB)Download full-size image
Co-reporter:Jianfang Jiang;Jingwen Liang;Shan Zhao;Yunfeng Wang
Journal of Cluster Science 2017 Volume 28( Issue 3) pp:971-982
Publication Date(Web):2017 May
DOI:10.1007/s10876-016-1092-x
Four new Organooxotin Clusters: [(p-MeC6H4)Sn(O)L1]6 (1) (HL1 = 2-(9H-carbazol-9-yl)acetic acid), [PhSn(O)L2]6·2C6H6·2H2O (2) (HL2 = 3-(9H-carbazol-9-yl)propanoic acid), [n-BuSn(O)L2]6 (3), [(c-Hex2Sn)2(L1)O(OH)]2·3C6H6 (4), were synthesized with benzene being used as solvent in the reaction and characterized by elemental analysis, IR, NMR spectroscopy and X-ray crystallography diffraction analyses. Complexes 1–3 are hexanuclear organotin complexes with drum structure. Complex 4 is dimeric carboxylate tetraorganodistannoxane and shows a ladder structure. There are four crystallographically unique Sn centers in the structure of 4, which consists of a Sn4O2(OH)2 ladder unit, and the ladder consists of four tins held together by four µ3-oxygens. All the complexes show an extensive supramolecular organization in the solid state and form 1D or 2D supramolecular assembly mediated by C–H…O, C–H…π or π…π interactions. Moreover, complexes 1 and 4 exhibit good fluorescence properties in the solid state revealed by the luminescent investigation. The experimental results show the complexes may be explored for potential luminescent materials.
Co-reporter:Xiaoning Song, Shuangquan Tian, Ziming Zhao, Dongsheng Zhu, and Mang Wang
Organic Letters 2016 Volume 18(Issue 14) pp:3414-3417
Publication Date(Web):July 1, 2016
DOI:10.1021/acs.orglett.6b01567
A highly controlled ring opening of siloxydifluorocyclopropanes, formed by nBuN4Br-catalyzed difluorocyclopropanation of methyl vinyl ketones bearing a β-alkylthio group by using TMSCF2Br as a unique difluorocarbene source, results in metal difluorohomoenolates with assistance of copper or silver followed by an intramolecular addition and elimination reaction leading to α-gem-difluorocyclopentenones efficiently.
Co-reporter:Xiaoning Song, Jian Chang, Dongsheng Zhu, Jiaheng Li, Cong Xu, Qun Liu, and Mang Wang
Organic Letters 2015 Volume 17(Issue 7) pp:1712-1715
Publication Date(Web):March 23, 2015
DOI:10.1021/acs.orglett.5b00488
A unique domino reaction of enolizable carbonyl compounds with Me3SiCF2Br to construct α-fluoroenones and α-fluoroenals is described to undergo the in situ formation of difluorocarbene and silyl enol ether, difluorocyclopropanation, desilylation, ring-opening, and defluorination sequence. In this tandem reaction, Me3SiCF2Br acts as not only the difluorocarbene source but also the TMS transfer agent as well as internal bromide and fluoride anion catalyst. It allows the transformations to occur smoothly under only a catalytic amount of n-Bu4NBr as initiator.
Co-reporter:Jian Chang, Xiaoning Song, Wanqiao Huang, Dongsheng Zhu and Mang Wang
Chemical Communications 2015 vol. 51(Issue 84) pp:15362-15365
Publication Date(Web):03 Sep 2015
DOI:10.1039/C5CC06825H
A direct method for the synthesis of o-fluoronaphthols and o/p-fluorophenols has been developed by a catalytic ring expansion of indanones and 2-cyclopentenones, in which TMSCF2Br was used as a unique :CF2 source, a TMS transfer agent, as well as the Br− and F− releaser for the enolization, difluorocyclopropanation, desilylation, ring opening, defluorination, and aromatization sequence.
Co-reporter:Aboubacar Sidiki Sougoule;Xiao Xiao;Cheick Abdoul Balde;Adama Moussa Sakho
Heteroatom Chemistry 2015 Volume 26( Issue 4) pp:270-276
Publication Date(Web):
DOI:10.1002/hc.21257
ABSTRACT
An organotin carboxylate based on amide carboxylic acid (Ph3Sn)(L)·C7H8 (complex 1) (HL = 3-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)propanoic acid) has been synthesized and characterized by elemental analyses (IR, 1H, 13C, and 119Sn NMR), UV–visible spectroscopies, and X-ray crystallography diffraction analysis. Complex 1 is a monomeric triphenyltin carboxylate. Ligand HL in complex 1 adopts unidentate coordination mode. Intermolecular hydrogen bonds and CH···π interactions help complex 1 to build fascinating one-dimensional and two-dimensional structures, which are discussed in detail.
Co-reporter:Aboubacar Sidiki Sougoule;Cheick Abdoul balde;Namory Keita;Xiao Xiao;Xiao Han;Jingwen Liang
Heteroatom Chemistry 2015 Volume 26( Issue 5) pp:382-390
Publication Date(Web):
DOI:10.1002/hc.21271
ABSTRACT
A new tetranuclear organotin carboxylate {[(n-Bu2SnO)2L]2}n (complex 1) was synthesized by the reaction of di-n-butyltin oxide with (p-carboxymethoxy-phenoxy) acetic acid (LH2) and characterized by elemental analyses: IR, UV–visible, 1H, 13C, 119Sn NMR spectroscopy and single crystal X-ray study. X-ray crystallography diffraction data revealed that the complex 1 was polymeric fashion with a chain structure containing a ladder-like tetranuclear organo-oxotin cluster. In the complex 1, the ligand LH2 is coordinated to the central tin(IV) atoms via the carboxylato-O atoms. The tetranuclear tin system is formed by the bridges through the carbonyl oxygen atom of the carboxylate moieties and making the tin atom of pentacoordinated in distorted trigonal bipyramidal geometry. Single crystal X-ray data indicate that the complex 1 crystallized in the cubic system with the space group C2/c.
Co-reporter:Gang Zheng, Xiaoli Ma, Jiaheng Li, Dongsheng Zhu, and Mang Wang
The Journal of Organic Chemistry 2015 Volume 80(Issue 17) pp:8910-8915
Publication Date(Web):August 7, 2015
DOI:10.1021/acs.joc.5b01468
A direct N-trifluoromethylation method has been developed by the use of the in situ generated [ArICF3]+ species as the electrophilic trifluoromethyl source. Upon treatment of N–H ketimines with Ruppert–Prakash reagent in the presence of PhI(OAc)2 and KF, or with Togni’s reagent II catalyzed by copper salt, N-trifluoromethylated imine products were obtained in moderate to good yields.
Co-reporter:Xiao Xiao, Lisong Yan, Zemin Mei, Dongsheng Zhu and Lin Xu
RSC Advances 2014 vol. 4(Issue 6) pp:3096-3101
Publication Date(Web):03 Dec 2013
DOI:10.1039/C3RA46198J
Two novel macrocyclic organotin(IV) carboxylates [(n-Bu2Sn)L1]2•C7H8 (1) (L1 = 2-(4-carboxyphenylcarbamoyl)benzoic acid) and [(n-Bu2Sn)L2]3•H2O (2) (L2 = 5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-isophthalic acid) were generated by the reactions of dibutyltin oxide with amide dicarboxylic acids and characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy. X-ray crystallography diffraction analyses reveal that 1 is a di-nuclear dicarboxylate ring and 2 is a trinuclear tricarboxylate macrocycle. With the help of intermolecular interactions, 1 and 2 construct supramolecular 3D architectures filled with cavities. Free toluene and water molecules are located in the cavities of 1 and 2 respectively as guests. Thermal analyses suggest that complex 2 is thermally more stable than 1. The antitumour activity of 1 and 2 has also been studied.
Co-reporter:Aboubacar Sidiki Sougoule, Zemin Mei, Xiao Xiao, Cheick Abdoul Balde, Salematou Samoura, Arouna Dolo, Dongsheng Zhu
Journal of Organometallic Chemistry 2014 Volume 758() pp:19-24
Publication Date(Web):15 May 2014
DOI:10.1016/j.jorganchem.2014.01.034
•One organotin carboxylate based on amide carboxylic acid was synthesized.•It is a macrocycle contains one penta-nuclear four-fold-ladder-like organo-oxotin unit.•Its synthesis, characterizations and crystal structure are discussed in detail.A novel macrocyclic organotin carboxylate [(n-Bu2SnO)5L] (complex 1) [H2L = (3-carboxymethoxy-phenoxy) acetic acid] was synthesized by the reaction of di-n-butyltin oxide with H2L and is characterized by elemental analyses i.e. IR 1H NMR and UV spectroscopies. X-ray crystallography diffraction analysis reveals that complex 1 is a centrosymmetric macrocycle and contains a penta-nuclear four-fold-ladder-like organo-oxotin cluster. All five Sn atoms are five-coordinated and the coordination environment can be considered as a trigonal bipyramidal. The luminescent property of complex 1 has also been investigated. Pilot studies have confirmed that complex 1 has shown good antitumor activity.A 16-membered unusual macrocycle with a single-ladder and containing one penta-nuclear four-fold-ladder-like organo-oxotin unit was synthesized. It has been full characterized. The preliminary fluorescent property and antitumor activity of it have also been investigated.
Co-reporter:Jingwen Liang, Dafeng Du, Xiao Xiao, Xiao Han, Dongsheng Zhu, Zemin Mei
Inorganic Chemistry Communications 2014 40() pp: 133-137
Publication Date(Web):
DOI:10.1016/j.inoche.2013.12.001
Co-reporter:Xiao Xiao, Kuizhan Shao, Lisong Yan, Zemin Mei, Dongsheng Zhu and Lin Xu
Dalton Transactions 2013 vol. 42(Issue 43) pp:15387-15390
Publication Date(Web):19 Aug 2013
DOI:10.1039/C3DT50531F
A novel macrocyclic organotin(IV) carboxylate {[n-Bu2Sn(O)]9(CH2CH3)2L}·3CH2CH3OH (complex 1) (L = (9-carboxymethyl-1,3,8,10-tetraoxo-3,8,9,10-tetrahydro-1H-anthra[2,1,9-def;6,5,10-d′e′f′]diisoquinolin-2-yl)-acetic acid) was generated by the reaction of dibutyltin oxide with amide dicarboxylic acid L and characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy. X-ray crystallography diffraction analysis reveals that 1 is a centrosymmetric macrocycle and contains a nona-nuclear eight-fold-ladder-like organo-oxotin cluster. The preliminary luminescent properties of complex 1 have also been studied.
Co-reporter:Xiao Xiao, Xiao Han, Zemin Mei, Dongsheng Zhu, Kuizhan Shao, Jingwen Liang, Min Tian, Lin Xu
Journal of Organometallic Chemistry 2013 729() pp: 28-39
Publication Date(Web):
DOI:10.1016/j.jorganchem.2013.01.017
Co-reporter:Li Yan;Chuan-Bi Li;Dong-Sheng Zhu;Lin Xu
Journal of Inorganic and Organometallic Polymers and Materials 2012 Volume 22( Issue 2) pp:395-403
Publication Date(Web):2012 March
DOI:10.1007/s10904-011-9591-6
Two novel metal–organic coordination polymers {[Pb2(MIP)2(BDC)2]·H2O}n1 and [Cd(MIP)(NDC)]n2 [MIP = 2-(3-methoxyphenyl)-1H-imidazo [4,5-f] [1, 10] phenanthroline, BDC = terephthalic acid, NDC = naphthalene-1,4-dicarboxylic acid] were obtained from hydrothermal reaction and characterized by elemental analysis, thermogravimetric (TG) analysis, infrared spectrum (IR) and single-crystal X-ray diffraction. The coordination polymers crystallize in triclinic, space group P-1 with a = 1.0335(2), b = 1.4224(3), c = 1.8156(4) nm, β = 106.088(3)° for complex 1 and the complex 2 crystallizes in monoclinic, space group P2(1)/n with a = 1.2562(8), b = 1.4800(9), c = 1.3723(8) nm, β = 97.257(1)°, respectively. The metal ions Pb(II) are located in [:PbN2O4] pentagonal bipyramidal geometry in complex 1. The metal ions Cd(II) in complex 2 act as distorted octahedral geometry, being surrounded by four carboxylate oxygen atoms from three NDC ligands and two donor nitrogen atoms from one MIP molecule. Moreover, there are hydrogen bonds in the two complexes, and it is noteworthy that the existence of hydrogen bonds and π–π interactions reinforce the structural stability of the title complexes, which have been proved by TG analysis. The luminescent properties for the ligand MIP, NDC and complex 2 are also discussed in detail.
Co-reporter:Xiao Xiao, Dafeng Du, Min Tian, Xiao Han, Jingwen Liang, Dongsheng Zhu, Lin Xu
Journal of Organometallic Chemistry 2012 715() pp: 54-63
Publication Date(Web):
DOI:10.1016/j.jorganchem.2012.05.038
Co-reporter:Xiao Xiao, Dafeng Du, Xiao Han, Jingwen Liang, Min Tian, Dongsheng Zhu, Lin Xu
Journal of Organometallic Chemistry 2012 713() pp: 143-150
Publication Date(Web):
DOI:10.1016/j.jorganchem.2012.05.001
Co-reporter:Chunling Liu, Shuangshuang Liu, Dafeng Du, Dongsheng Zhu, Lin Xu
Journal of Molecular Structure 2011 Volume 1003(1–3) pp:134-140
Publication Date(Web):28 September 2011
DOI:10.1016/j.molstruc.2011.07.052
Two organotin(IV) carboxylates of (E)-3-(2-nitrophenyl) propenoic acid (HL), [Ph3SnL]n (1) and {[Bu2SnL]2O}2 (2), have been synthesized. All the complexes were characterized by elemental analysis, FT-IR and NMR (1H, 13C) spectroscopy. In addition, the molecular structures of 1 and 2 have been determined by single crystal X-ray diffraction analysis. Complex 1 consisted of a 1D chain polymer and was interconnected by CH⋯π stacking to aggregate in 2D framework. Complex 2 contained a dimeric tetraorganodistannoxane of ladder arrangement and was linked by CH⋯O hydrogen bonds to form a 1D chain. Their antitumor activities were also investigated.Highlights► Di- and tri-organotin carboxylates are synthesized. ► We report their structural characterization and antitumor activities. ► CH⋯π stacking and CH⋯O interaction stabilize the molecular structures. ► Triorganotin carboxylate displays a higher biological activity.
Co-reporter:Chunling Liu, Wenjie Li, Dafeng Du, Dongsheng Zhu, Lin Xu
Journal of Molecular Structure 2011 Volume 994(1–3) pp:263-268
Publication Date(Web):17 May 2011
DOI:10.1016/j.molstruc.2011.03.029
The reaction of triphenyltin (IV) hydroxide with the naphthalimide derivatives, 5-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-isophthalic acid (H2L1) and 4-(1,3-dioxo-1H,3H-benzo[de]isoquinolin-2-yl)-benzoic acid (HL2) yielded the complexes [(SnPh3)2L1·2C7H8] (1), and [(SnPh3)L2] (2), respectively. All complexes were characterized by elemental analysis, FT-IR, NMR (1H, 13C) spectroscopy and X-ray crystallography diffraction analysis to elucidate their structures both in solution and in solid state. The structural analysis showed that complexes 1 and 2 were monomeric structures and further interlinked by intermolecular CH⋯O hydrogen bonds. The molecule of 1 was linked by CH⋯O hydrogen bonds into a 1D chain, which was also interconnected by CH⋯O interactions to aggregate in 2D framework. In complex 2, two molecules of 2 linked by CH⋯O hydrogen bonds formed a 12-membered ring. Additionally, these rings were connected via other intermolecular hydrogen bonds into a 1D chain. Their thermal stabilities were also investigated.Highlights► We synthesize two triphenyltin carboxylates with naphthalimide derivatives. ► We characterize their structures and investigate their thermal stabilities. ► The hydrogen bonding interactions play key roles in supramolecular structures.
Co-reporter:Li Yan, Chuanbi Li, Dongsheng Zhu, Lin Xu
Journal of Molecular Structure 2011 Volume 1002(1–3) pp:172-178
Publication Date(Web):14 September 2011
DOI:10.1016/j.molstruc.2011.07.025
Two novel complexes [Cd2(MIP)2(BDC)2]n (1) [MIP = 2-(3-methoxyphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline, BDC = terephthalic acid] and [Cd(IPM)(NDC)]n (2) [IPM = 4-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl)-2-methoxyphenol, NDC = naphthalene-1,4-dicarboxylic acid] have been synthesized by hydrothermal reaction and characterized by elemental analysis, IR, single-crystal X-ray diffraction and thermogravimetric analysis (TGA). Complex 1 exhibits 1D zigzag chain structure and complex 2 shows 2D layer topology. The intermolecular CH⋯O interactions extend the complex 1 into 2D networks, and the existing H-bonds further stabilized the complexes 1–2, which can be proved by TGA experiment. Furthermore, the solid-state fluorescence spectrum of the complex 2 was studied, as well as the ligand IPM. The complex 2 exhibits intense broad emission at 540 nm at room temperature, which is red-shifted by 45 nm relative to that of free ligand IPM.Highlights► We synthesized two novel Cd(II) complexes by hydrothermal reaction. ► The hydrogen bonding interactions play key roles in supramolecular structures. ► We studied the solid-state fluorescence of complex 2, as well as the ligands.
Co-reporter:Dafeng Du, Zijiang Jiang, Chunling Liu, Adama Moussa Sakho, Dongsheng Zhu, Lin Xu
Journal of Organometallic Chemistry 2011 696(13) pp: 2549-2558
Publication Date(Web):
DOI:10.1016/j.jorganchem.2011.03.048
Co-reporter:Adama Moussa Sakho;Dafeng Du;Wenjie Li;Shuangshuang Liu;Lin Xu
Heteroatom Chemistry 2010 Volume 21( Issue 5) pp:304-313
Publication Date(Web):
DOI:10.1002/hc.20614
Abstract
Three new organotin(IV) carboxylates of composition [(R)2Sn(O2CC6H4C-OC6H4CH3)2] 1, [(R)2Sn(O2CC6H4COC6H4-C2H5)2]22, and R3SnO2 CC6H4COC6H4CH33, were obtained by reactions of (R)2SnO [R = o-tolyl] with 2-(4-methyl benzoyl) benzoic acid and 2-(4-ethyl benzoyl) benzoic acid, and reaction of Cy3SnOH [Cy = cyclohexyl] with 2-(4-methyl benzoyl) benzoic acid, respectively. The complexes 1, 2 and 3 have been characterized by elemental analysis, infrared (IR), 1HNMR, and X-ray crystallography diffraction analyses. The complex 1 has two folded symmetrical structure; the tin atom in 1 is found to adopt a distorted toward skew-trapezoidal bipyramidal geometry. Molecular structure of the complex 2 is centrosymmetric, and the internal tin atom is five-coordinated and is in distorted trigonal bipyramidal geometry. The crystal structure of the complex 3 is found to exhibit distorted tetrahedral geometry. Pilot studies have indicated that the complexes 1 and 2 have shown good antitumor activities. © 2010 Wiley Periodicals, Inc. Heteroatom Chem 21:304–313, 2010; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20614
Co-reporter:Wenjie Li, Dafeng Du, Shuangshuang Liu, Chaoguang Zhu, Adama Moussa Sakho, Dongsheng Zhu, Lin Xu
Journal of Organometallic Chemistry 2010 695(18) pp: 2153-2159
Publication Date(Web):
DOI:10.1016/j.jorganchem.2010.06.001
Co-reporter:Jian Chang, Xiaoning Song, Wanqiao Huang, Dongsheng Zhu and Mang Wang
Chemical Communications 2015 - vol. 51(Issue 84) pp:NaN15365-15365
Publication Date(Web):2015/09/03
DOI:10.1039/C5CC06825H
A direct method for the synthesis of o-fluoronaphthols and o/p-fluorophenols has been developed by a catalytic ring expansion of indanones and 2-cyclopentenones, in which TMSCF2Br was used as a unique :CF2 source, a TMS transfer agent, as well as the Br− and F− releaser for the enolization, difluorocyclopropanation, desilylation, ring opening, defluorination, and aromatization sequence.
Co-reporter:Xiao Xiao, Kuizhan Shao, Lisong Yan, Zemin Mei, Dongsheng Zhu and Lin Xu
Dalton Transactions 2013 - vol. 42(Issue 43) pp:NaN15390-15390
Publication Date(Web):2013/08/19
DOI:10.1039/C3DT50531F
A novel macrocyclic organotin(IV) carboxylate {[n-Bu2Sn(O)]9(CH2CH3)2L}·3CH2CH3OH (complex 1) (L = (9-carboxymethyl-1,3,8,10-tetraoxo-3,8,9,10-tetrahydro-1H-anthra[2,1,9-def;6,5,10-d′e′f′]diisoquinolin-2-yl)-acetic acid) was generated by the reaction of dibutyltin oxide with amide dicarboxylic acid L and characterized by elemental analysis, IR, 1H and 13C NMR spectroscopy. X-ray crystallography diffraction analysis reveals that 1 is a centrosymmetric macrocycle and contains a nona-nuclear eight-fold-ladder-like organo-oxotin cluster. The preliminary luminescent properties of complex 1 have also been studied.