Co-reporter:Shiming Bi, Yankai Li, Limin Wang, Jun Hu, and Honglai Liu
The Journal of Physical Chemistry C March 30, 2017 Volume 121(Issue 12) pp:6685-6685
Publication Date(Web):March 9, 2017
DOI:10.1021/acs.jpcc.6b12534
To obtain solid scaffolds exhibiting brilliant solid state fluorescence and serving as an arena for chromo communication via host–guest energy transfer, a series of diketopyrrolopyrrole moieties with different modified bulky groups were coupled into the porous polymeric networks via Sonogashira coupling reaction. Variation of the bulky substitution groups rendered the tunability of porosity. With the improved porosity, it triggered the spatial isolation of the fluorophores and further enhanced the solid-state fluorescence of these polymers. More importantly, the brilliant nanopores can also serve to confine guest molecules to form a donor–acceptor system via energy transfer. After loading coumarin, outstanding energy transfer efficiency, was observed based on the calculation upon fluorescence decay measurements, spectral overlap function and the estimation of Föster radius. This study provided important insights of designing novel fluorescent POPs with efficient energy transfer flows.
Co-reporter:Biao Chen, Jie Xu, Limin WangLongfeng Song, Shengying Wu
ACS Applied Materials & Interfaces 2017 Volume 9(Issue 8) pp:
Publication Date(Web):January 31, 2017
DOI:10.1021/acsami.6b15400
A series of DPP derivatives bearing quaternary ammonium salt centers with different lengths of carbon chains have been designed and synthesized. Their inhibition actions on copper electroplating were first investigated. A total of four diketopyrrolopyrrole (DPP) derivatives showed different inhibition capabilities on copper electroplating. To investigate interactions between metal surface and additives, we used quantum chemical calculations. Static and dynamic surface tension of four DPP derivatives had been measured, and the results showed DPP-10C (1c) with a faster-decreasing rate of dynamic surface tension among the four derivatives, which indicated higher adsorption rate of additive on the cathode surface and gives rise to stronger inhibiting effect of copper electrodeposition. Then, DPP-10C (1c) as the representative additive, was selected for the systematic study of the leveling influence during microvia filling through comprehensive electroplating tests. In addition, field-emission scanning electron microscope images and X-ray diffraction results showed the surface morphology, which indicated that addition of DPP derivative (1c) could lead a fine copper deposit and cause the preferential orientations of copper deposits to change from [220] to [111], which happened in particular at higher concentrations.Keywords: diketopyrrolopyrrole; electroplating; leveler; microvia; quaternary ammonium salts;
Co-reporter:Jie Xu, Shaoze Zhang, Shengying Wu, Shiming Bi, Xinjin Li, Yunxiang Lu, Limin Wang
Tetrahedron 2017 Volume 73(Issue 5) pp:494-499
Publication Date(Web):2 February 2017
DOI:10.1016/j.tet.2016.12.021
We novelly designed and synthesized a set of fluorinated diphenyl-diketopyrrolopyrrole (DPP) compounds by varying the position and amount of fluorine atom, and to the best of our knowledge, it is the first time a difluoromethyl group and perfluoroalkyl chains had been introduced into the DPP unit in good yields. We investigate the optical/electrochemical properties of all the compounds. Density functional theory (DFT) calculations were applied to explore orbital energy value of these compounds. The results demonstrated that the perfluorocarbon chains substituted DPPs with larger red-shift in both absorption and emission spectra and narrower bandgap.
Co-reporter:Chen Hu;Gang Hong;Xiaofei Qian;Kwang Rim Kim;Xiaoyan Zhu;Limin Wang
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 23) pp:4984-4991
Publication Date(Web):2017/06/14
DOI:10.1039/C7OB01025G
A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.
Co-reporter:Jianwei Han, Xunshen Wu, Zhiang Zhang, Limin Wang
Tetrahedron Letters 2017 Volume 58, Issue 35(Issue 35) pp:
Publication Date(Web):30 August 2017
DOI:10.1016/j.tetlet.2017.07.065
•Palladium-catalyzed arylative cascades of ortho-aminocinnamate esters is developed.•4-Aryl quinolin-2(1H)-ones were synthesized in good to excellent yields.•Diaryliodonium salts was used as efficient arylating reagents.Palladium-catalyzed cascades of arylation/cyclization/desulfonation of ortho-aminocinnamate esters by using diaryliodonium salts afforded a wide range of 4-aryl quinolin-2(1H)-ones. As such, the desired 4-aryl quinolin-2(1H)-ones with potential biological activity has been synthesized in the yields of 34–96%.Download high-res image (47KB)Download full-size image
Co-reporter:Qiao Zhao;Kai Zhao;Sheng-ying Wu;Bo-xue Tian
Research on Chemical Intermediates 2017 Volume 43( Issue 3) pp:1689-1708
Publication Date(Web):16 September 2016
DOI:10.1007/s11164-016-2723-4
Factors leading to the formation of a hexahydroaporphine-like cyclizing side product were studied systematically for the first time and the ratio of this side product was controlled effectively. To understand better the electronic effect of substrates on the formation of side products, different 1-benzyloctahydroisoquinolines with substituted groups on nitrogen or benzene ring were compared. A plausible mechanism of cyclizing reaction was proposed, and key intermediates as well as transition states were analyzed using DFT calculations.
Co-reporter:Xinjin Li, Jingwei Zhao, Mingyou Hu, Dingben Chen, Chuanfa Ni, Limin Wang and Jinbo Hu
Chemical Communications 2016 vol. 52(Issue 18) pp:3657-3660
Publication Date(Web):01 Feb 2016
DOI:10.1039/C5CC10550A
A new method for the generation of the “PhSO2CF2Cu” species from readily available difluoromethyl phenyl sulfone (PhSO2CF2H) has been developed. The “PhSO2CF2Cu” reagent can be applied in (phenylsulfonyl)difluoromethylation of arylboronic acids, which affords a convenient approach to introducing the PhSO2CF2 group into aromatics.
Co-reporter:Shengying Wu, Zhijun Chen, Kewei Zhang, Gang Hong, Guosheng Zhao, Limin Wang
Tetrahedron Letters 2016 Volume 57(Issue 12) pp:1390-1395
Publication Date(Web):23 March 2016
DOI:10.1016/j.tetlet.2016.02.076
A simple 1,1′-bi-2-naphthol (1,1′-BINOL) boron complex has been rationally designed and synthesized, the structure of which was confirmed by single crystal X-ray diffraction analysis. Furthermore, the complex exhibited turn-on fluorescence for fluoride ions with high selectivity and sensitivity. The recognition mechanism for promoting was determined by 1H, 19F and 11B NMR titrations, which indicated that both the photo-induced electron-transfer (PET) and the intramolecular charge transfer (ICT) effects were functionalized. In addition, the complex showed strong solid-state fluorescence, and the emission spectrum and quantum efficiency (ΦF) of the solid powders were also measured.
Co-reporter:Yue Wu, Xiaofei Cai, Shengying Wu, Limin Wang, Guifeng Wang, Feng Wang
Tetrahedron Letters 2016 Volume 57(Issue 30) pp:3376-3378
Publication Date(Web):27 July 2016
DOI:10.1016/j.tetlet.2016.06.075
•A new epindolidion derivative applied as Hg2+ ion probe for the first time.•Colorimetric and ratiometric recognition with good selectivity and sensitivity.•Good linear property.After functionalization, a new epindolidion derivative bearing a vinyl group was synthesized as a naked-eye fluorescent probe for Hg2+ through two steps. The probe showed good selectivity to Hg2+ over other metal cations in CH3CN. On the basis of the addition of Hg2+, the fluorescence emission of the probe at 485 nm was ratio quenched along with the appearance of the new peak at 574 nm. Simultaneously, the absorbance of the probe showed bathochromic shift as a function of the increasing concentration of Hg2+. All of the features mentioned make this compound a useful probe for Hg2+ measurement. To the best of our knowledge, it’s the first fluorescent probe based on epindolidion.
Co-reporter:Xiaofei Qian, Jianwei Han, Limin Wang
Tetrahedron Letters 2016 Volume 57(Issue 5) pp:607-610
Publication Date(Web):3 February 2016
DOI:10.1016/j.tetlet.2015.12.100
The selective arylations of 2-naphthol and phenol derivatives catalyzed by Cu(OTf)2 with using diaryliodonium(III) salts have been developed. With this method, biaryls bearing hydroxyl groups can be easily accessed in moderate to good yields. Additionally, this protocol provided an alternative for the preparation of 3-arylated binaphthalene derivatives.
Co-reporter:Kewei Zhang, Shengying Wu, Dahui Qu, Limin Wang
Tetrahedron Letters 2016 Volume 57(Issue 10) pp:1133-1137
Publication Date(Web):9 March 2016
DOI:10.1016/j.tetlet.2016.01.101
A ratiometric BINOL-based fluorescent probe for Zn2+ detection was rationally designed and synthesized. Based on the excited-state intramolecular proton transfer (ESIPT) mechanisms, the probe exhibited a significant variation on emission wavelengths with shifts more than 100 nm after combining with Zn2+, with emission colors changing from yellow to blue. Good selectivity and sensitivity of the probe toward Zn2+ could be found in aqueous solution. Sensing mechanism was proposed on the basis of fluorescence, absorption, ESI mass spectrometry, IR spectra, and CD spectra.
Co-reporter:Gang Hong, Shengying Wu, Xiaoyan Zhu, Dan Mao, Limin Wang
Tetrahedron 2016 Volume 72(Issue 3) pp:436-441
Publication Date(Web):21 January 2016
DOI:10.1016/j.tet.2015.11.063
An efficient and metal-free method has been developed for the direct synthesis of amides from readily available azobenzenes reacting with aroyl surrogates such as alcohols, methylarenes. A variety of amides were afforded in moderate to good yields through this reaction. It is another example reported by our group for the use of azobenzene as the new radical acceptor.
Co-reporter:Ping Yu;Xingxing Zhu;Jidong Gao
Journal of Coatings Technology and Research 2016 Volume 13( Issue 6) pp:963-971
Publication Date(Web):2016 November
DOI:10.1007/s11998-016-9807-3
Dendritic–linear polyether-modified silica sol (DLPS) was synthesized using diethylenetriamine, methyl acrylate, epoxy-terminated polyether, triethoxysilane, and silica sol in five steps. The prepared sol was stable and transparent. DLPS was characterized by Fourier transform infrared spectroscopy, thermogravimetric analysis, and particle size distribution analysis. Subsequently, DLPS was examined as a stain-resistant additive in (paint) coatings. The surface of the sample coatings with and without DLPS additive was examined by scanning electron microscopy, energy-dispersive spectrometry analysis, and contact angle analysis. The results showed that the stain-resistant additive appeared on the surface of the coating, which made the surface more compact and hydrophilic. The performance of the stain-resistant additive was examined in commercial outdoor emulsion coatings (WB200). The result showed that the presence of the stain-resistant additive could enhance the stain resistance performance of paint. Furthermore, the stain resistance performance improved with increasing amounts of additive. Specifically, the stain resistance performance of paint improved by 40.63% in the presence of 6 wt% DLPS. Therefore, the current findings demonstrate the importance of DLPS in advancing progress and application in the paint coating industry.
Co-reporter:Gang Hong, Xiaoyan Zhu, Chen Hu, Alfred Njasotapher Aruma, Shengying Wu, and Limin Wang
The Journal of Organic Chemistry 2016 Volume 81(Issue 15) pp:6867-6874
Publication Date(Web):July 7, 2016
DOI:10.1021/acs.joc.6b01210
Addition of diarylphosphine oxides to the N═N double bond of azobenzenes leads to the formation of the P-substituted hydrazines in up to 98% yield for 24 examples, and the formation of diphenylphosphinic amides was observed in three substrates. This strategy features tolerance of a wide range of functional groups, simple operation, and mild reaction conditions. Specially, this method can be also applied to the gram-scale synthesis of the product. A polar reaction mechanism is also proposed based on control experiments.
Co-reporter:Xinjin Li;Dr. Jingwei Zhao;Yunze Wang;Jian Rong;Dr. Mingyou Hu;Dr. Dingben Chen;Pan Xiao;Dr. Chuanfa Ni;Dr. Limin Wang;Dr. Jinbo Hu
Chemistry – An Asian Journal 2016 Volume 11( Issue 12) pp:1789-1792
Publication Date(Web):
DOI:10.1002/asia.201600577
Abstract
A new method for the formation of 1,1-difluoroethyl copper species (“CuCF2CH3”) with 1,1-difluoroethylsilane (TMSCF2CH3) has been developed. The “CuCF2CH3” species can be applied to the efficient 1,1-difluoroethylation of diaryliodonium salts under mild conditions, affording (1,1-difluoroethyl)arenes in good to excellent yields. This convenient procedure tolerates a wide range of functional groups and thus serves as a practical synthetic tool for the introduction of CF2CH3 group(s) into complex molecules.
Co-reporter:Yankai Li, Shiming Bi, Fei Liu, Shengying Wu, Jun Hu, Limin Wang, Honglai Liu and Ying Hu
Journal of Materials Chemistry A 2015 vol. 3(Issue 26) pp:6876-6881
Publication Date(Web):26 May 2015
DOI:10.1039/C5TC00682A
Most organic dyes dissipate their excitation energy in the aggregated state because of the “aggregation-caused quenching” effect, deteriorating their application in optoelectronic devices. To prevent the “aggregation-caused quenching” effect, we incorporate a dye-based fluorophore into a porous organic polymer skeleton because porosity would allow the spatial isolation of fluorophores to maintain their emission. Tuning the fraction of fluorophores in the skeleton of FL-SNW-DPPs could spread the emission color coverage from red to blue in both solid-state and suspension. More importantly, the combination of fluorescence and porosity of FL-SNW-DPPs would provide more space to transduce the molecular interaction between adsorbed analytes and fluorophores to the detectable changes in light emission, leading to the fluorescence-off or fluorescence-on detection of electron-deficient or electron-rich analytes.
Co-reporter:Xunshen Wu, Yang Yang, Jianwei Han, and Limin Wang
Organic Letters 2015 Volume 17(Issue 22) pp:5654-5657
Publication Date(Web):November 2, 2015
DOI:10.1021/acs.orglett.5b02938
With a strategy that makes use of palladium activation of both C–I and vicinal C–H bonds of diaryliodonium salts, an unprecedented approach in diarylation of coumarins was reported. As such, a wide range of 4,5-benzocoumarins with potential fluorescence properties have been synthesized in good yields. A series of experiments suggested that the formation of two carbon–carbon bonds proceeded in a synergetic manner.
Co-reporter:Xing Gao, Jianwei Han, and Limin Wang
Organic Letters 2015 Volume 17(Issue 18) pp:4596-4599
Publication Date(Web):September 9, 2015
DOI:10.1021/acs.orglett.5b02323
A new family of tartaric acid derived chiral iminophosphoranes has been developed as highly effective organocatalysts in the asymmetric chlorinations of 3-substituted oxindoles with a high level of enantioselectivity. Importantly, these catalysts are air- and moisture-stable. Recovery of the catalyst after simple chromatographic separation for reuse in the model reaction was achieved; the catalyst can be recycled six times without loss of any enantioselectivity. Several advantages of this catalytic process are high conversion after a very short reaction time at ambient temperature, low catalytic loading, and scale-up to multigram quantities with an excellent enantiomeric excess value of >99%, which meets the enantiomeric purity required for pharmaceutical purposes.
Co-reporter:Xinjin Li, Jingwei Zhao, Liang Zhang, Mingyou Hu, Limin Wang, and Jinbo Hu
Organic Letters 2015 Volume 17(Issue 2) pp:298-301
Publication Date(Web):December 26, 2014
DOI:10.1021/ol5034018
A new method for the generation of trifluoromethylcopper (“CuCF3”) species from readily available phenyl trifluoromethyl sulfoxide has been developed. The “CuCF3” reagent can be applied in efficient trifluoromethylations of aryl iodides and activated aryl bromides in the absence of additional ligands. Furthermore, the “CuCF3” species can also undergo oxidative cross-coupling with terminal alkynes and arylboronic acids.
Co-reporter:Dan Mao, Jun Tang, Wenbo Wang, Xin Liu, Shengying Wu, Jianjun Yu and Limin Wang
Organic & Biomolecular Chemistry 2015 vol. 13(Issue 7) pp:2122-2128
Publication Date(Web):03 Dec 2014
DOI:10.1039/C4OB02220C
An unexpected Sc(OTf)3-catalyzed and air-mediated cascade reaction of o-aminoacetophenones with methanamines was discovered as an efficient synthetic approach to a novel class of fluorescent fused-four-ring dibenzo[b,h][1,6]naphthyridine derivatives. Two possible mechanisms of the reaction were proposed. The photophysical properties of the dibenzo[b,h][1,6]naphthyridine 1a were initially considered.
Co-reporter:Song Mao, Xu Geng, Yang Yang, Xiaofei Qian, Shengying Wu, Jianwei Han and Limin Wang
RSC Advances 2015 vol. 5(Issue 46) pp:36390-36393
Publication Date(Web):17 Apr 2015
DOI:10.1039/C5RA03819G
A metal-free approach for the C4-arylation of 4-substituted-pyrazolin-5-ones with diaryliodonium salts was developed. The reaction proceeded smoothly at room temperature in the presence of DMAP (4-dimethylaminopyridine). As a result, a wide range of desired multi-substituted pyrazolin-5-one derivatives were obtained in good to excellent yields (20–98%).
Co-reporter:Lei Fang;Liangshun Chen;Jianjun Yu;Limin Wang
European Journal of Organic Chemistry 2015 Volume 2015( Issue 9) pp:1910-1914
Publication Date(Web):
DOI:10.1002/ejoc.201403479
Abstract
A catalytic amount of benzoyl peroxide (BPO)-initiated cross-dehydrogenative coupling reaction of N-iminopyridine ylides with simple alkanes and alcohols leads to the corresponding 2-alkylpyridines with high regioselectivity in moderate to good yields without an additional reduction step to remove the activated group.
Co-reporter:Yang Yang, Jianwei Han, Xunshen Wu, Shujia Xu, Limin Wang
Tetrahedron Letters 2015 Volume 56(Issue 24) pp:3809-3812
Publication Date(Web):10 June 2015
DOI:10.1016/j.tetlet.2015.04.082
The palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamate ester derivatives by using diaryliodonium(III) salts has been developed. With this method, 4-arylcoumarins were easily prepared in good to excellent yields under base-free conditions. Additionally, this protocol provided an efficient alternative for the preparation of related 4-arylated coumarin compounds which are useful in the access to 5-lipoxygenase inhibitors.An efficient method for the palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamate ester derivatives with diaryliodonium salts is described. A range of 4-arylcoumarins are obtained in good to excellent yield. Furthermore, the route can be applied to the synthesis of versatile building block of 5-lipoxygenase inhibitor.
Co-reporter:Mengyun Zhu, Jinqian Liu, Jianjun Yu, Liangshun Chen, Chunmei Zhang, and Limin Wang
Organic Letters 2014 Volume 16(Issue 7) pp:1856-1859
Publication Date(Web):March 17, 2014
DOI:10.1021/ol500136x
An unprecedented AlCl3-promoted formal [2 + 3]-cycloaddition of 1,1-cyclopropanes with readily available N-benzylic sulfonamides has been developed. Experimental evidence supports an unusual mechanism wherein the donor–acceptor cyclopropane serves as a source of 2-styrylmalonate rather than the “classical” 1,3-dipole. A broad range of 1,1-cyclopropanediesters undergo a carbocation-initiated cyclization reaction with N-benzylic sulfonamides to afford highly functionalized Indane derivatives in a fast and high-yielding procedure.
Co-reporter:Guanjun Zhang, Longfeng Song, Shiming Bi, Yue Wu, Jianjun Yu, Limin Wang
Dyes and Pigments 2014 Volume 102() pp:100-106
Publication Date(Web):March 2014
DOI:10.1016/j.dyepig.2013.10.025
•A series of functionalized diketopyrrolopyrrole were designed and synthesized.•A novel route was presented to adding OH group to diketopyrrolopyrrole.•The absorption and emission show gradual red-shift with electron-donation increase.•The diketopyrrolopyrroles have potential application in the synthesis of novel organic functional materials.•Increase of water-solubility by addition of oligoethyleneglycol chains opened the way to biological science.A series of symmetrically substituted diketopyrrolopyrrole derivatives were synthesized under mild conditions in good yields. All of the diketopyrrolopyrroles were characterized by 1H and 13C NMR, ultraviolet–visible and fluorescence spectroscopy, high resolution mass spectrometry and elemental analysis. The maximum absorption and emission bands showed gradual red-shift with the increase in electron donating strength of the 3,6-substituent. In addition, the optical properties of 4,4′-(2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)-3,6-dioxo-2,3,5,6-tetrahydropyrrolo[3,4-c]pyrrole-1,4-diyl)dibenzoic acid and 3,6-bis(4-hydroxyphenyl)-2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione were investigated under alkaline conditions. The results demonstrated that 3,6-bis(4-hydroxyphenyl)-2,5-bis(2-(2-(2-methoxyethoxy)ethoxy)ethyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione could be employed as an acid–base indicator. These diketopyrrolopyrroles derivatives have potential application in the synthesis of novel organic optoelectronic materials and in biological systems as a consequence of the increased water solubility.
Co-reporter:Zhaoyu Fan, Astrid Tay, Marc Pera-Titus, Wen-Juan Zhou, Samy Benhabbari, Xiaoshuang Feng, Guillaume Malcouronne, Laurent Bonneviot, Floryan De Campo, Limin Wang, Jean-Marc Clacens
Journal of Colloid and Interface Science 2014 Volume 427() pp:80-90
Publication Date(Web):1 August 2014
DOI:10.1016/j.jcis.2013.11.047
•Glycerol/dodecanol emulsions were prepared using amphiphilic silica particles.•The particles contained a combination of alkyl and sulfonic acid surface groups.•The droplet size was reduced until a concentration of 1 wt.% of silica particles.•Ostwald ripening and flocculation were the main destabilization mechanisms.•The particles catalyzed the etherification of glycerol with dodecanol at 150 °C.A key challenge in biomass conversion is how to achieve valuable molecules with optimal reactivity in the presence of immiscible reactants. This issue is usually tackled using either organic solvents or surfactants to promote emulsification, making industrial processes expensive and not environmentally friendly. As an alternative, Pickering emulsions using solid particles with tailored designed surface properties can promote phase contact within intrinsically biphasic systems. Here we show that amphiphilic silica nanoparticles bearing a proper combination of alkyl and strong acidic surface groups can generate stable Pickering emulsions of the glycerol/dodecanol system in the temperature range of 35–130 °C. We also show that such particles can perform as Pickering Interfacial Catalysts for the acid-catalyzed etherification of glycerol with dodecanol at 150 °C. Our findings shed light on some key parameters governing emulsion stability and catalytic activity of Pickering interfacial catalytic systems. This understanding is critical to pave the way toward technological solutions for biomass upgrading able to promote eco-efficient reactions between immiscible organic reagents with neither use of solvents nor surfactants.Graphical abstract
Co-reporter:Liangshun Chen;Hongyue Lang;Lei Fang;Mengyun Zhu;Jinqian Liu;Jianjun Yu;Limin Wang
European Journal of Organic Chemistry 2014 Volume 2014( Issue 23) pp:4953-4957
Publication Date(Web):
DOI:10.1002/ejoc.201402475
Abstract
An efficient method for the construction of two distinct Caryl–Caryl bonds through the Ni-catalyzed Suzuki–Miyaura cross-coupling of phenols with arylboronic acids has been developed. This reaction proceeds through the in situ tosylation of phenols by using N,N-ditosylaniline as the sulfonylating reagent, which is highly active, markedly stable, and easily prepared. The scope with respect to the coupling partners – phenols and boronic acids – is broad, and sensitive functional groups are tolerated. Phenols, especially those containing an unprotected amino group, which are generally problematic for coupling under conventional one-pot conditions, are also viable substrates in this transformation.
Co-reporter:Dan Mao;Gang Hong;Shengying Wu;Xin Liu;Jianjun Yu ;Limin Wang
European Journal of Organic Chemistry 2014 Volume 2014( Issue 14) pp:3009-3019
Publication Date(Web):
DOI:10.1002/ejoc.201400073
Abstract
Lewis-acid-catalyzed benzylic reactions of 2-methylazaarenes with aldehydes have been investigated. Series of azaarene derivatives were afforded by this reaction. 2-(Pyridin-2-yl)ethanols with common substituents were formed through the LiNTf2-promoted aldol reaction for the first time. 2-Alkenylpyridines, exclusively in the form of the E isomers, were synthesized in the presence of LiNTf2 cooperated with H2NTf. In the presence of La(Pfb)3 as catalysis, 2-alkenylquinolines were obtained in high yields through the reactions between 2-methylquinolines and aldehydes under air.
Co-reporter:Yang Yang;Xunshen Wu;Jianwei Han;Song Mao;Xiaofei Qian;Limin Wang
European Journal of Organic Chemistry 2014 Volume 2014( Issue 31) pp:6854-6857
Publication Date(Web):
DOI:10.1002/ejoc.201402920
Abstract
A transition-metal-free approach for the arylation of hydroxylamines and oximes with diaryliodonium salts was developed. The reaction proceeded smoothly at room temperature in the presence of cesium carbonate. As a result, a wide range of N- and O-arylated hydroxylamines were synthesized in good to excellent yields (45–98 %).
Co-reporter:Liangshun Chen;Hongyue Lang;Lei Fang;Jianjun Yu;Limin Wang
European Journal of Organic Chemistry 2014 Volume 2014( Issue 29) pp:6385-6389
Publication Date(Web):
DOI:10.1002/ejoc.201402919
Abstract
A nickel-catalyzed approach for the synthesis of biaryl compounds from N,N-disulfonylmethylamines and arylboronic acids has been developed. Instead of arenesulfonyl chlorides, various N,N-disulfonylmethylamines were used as the aryl source through extrusion of SO2 to give cross-coupling products in moderate to good yields.
Co-reporter:Xu Geng, Song Mao, Liangshun Chen, Jianjun Yu, Jianwei Han, Jianli Hua, Limin Wang
Tetrahedron Letters 2014 Volume 55(Issue 29) pp:3856-3859
Publication Date(Web):16 July 2014
DOI:10.1016/j.tetlet.2014.05.082
An efficient copper-catalyzed N-arylation of N-arylsulfonamides with diaryliodonium salts is reported. The reaction employs diaryliodonium salts and N-arylsulfonamides in water at room temperature, giving the products in moderate to excellent yields.
Co-reporter:Shengying Wu, Kewei Zhang, Yefeng Wang, Dan Mao, Xin Liu, Jianjun Yu, Limin Wang
Tetrahedron Letters 2014 Volume 55(Issue 2) pp:351-353
Publication Date(Web):8 January 2014
DOI:10.1016/j.tetlet.2013.11.024
Naphthalimide and BINOL framework based fluorescent probe NP-B was rationally designed and synthesized. NP-B exhibited ‘turn-on’ fluorescence for Cr3+ and high selectivity over other metal ions. 1:1 binding mode between NP-B and Cr3+ was proposed and the mode was verified through MALDI-TOF mass spectrum. The detection limit was calculated to be 0.20 μM, which indicated the good sensitivity for Cr3+.
Co-reporter:Yefeng Wang, Liang Zhang, Guanjun Zhang, Yue Wu, Shengying Wu, Jianjun Yu, Limin Wang
Tetrahedron Letters 2014 Volume 55(Issue 21) pp:3218-3222
Publication Date(Web):21 May 2014
DOI:10.1016/j.tetlet.2014.03.137
A perylene bisimide derivative (PBI) based colorimetric and fluorescent bifunctional probe PAM-PBI was designed and synthesized. It was highly selective and sensitive for distinguishing both Cu2+ and F− from other ions through a conspicuous change of UV–vis and fluorescence spectra. The recognition of Cu2+ by PAM-PBI showed an obvious color change from rose red to purple in aqueous solution, while the sensing of F− gave a marked color change from rose red to light green in THF.
Co-reporter:Gang Hong, Dan Mao, Shengying Wu, and Limin Wang
The Journal of Organic Chemistry 2014 Volume 79(Issue 21) pp:10629-10635
Publication Date(Web):October 8, 2014
DOI:10.1021/jo501928x
An efficient palladium-catalyzed regioselective C–P bond formation of azo compounds through C–H bond functionalization using dialkyl phosphites as phosphorus source under mild conditions was developed. A series of both symmetrical and unsymmetrical azoarenes were successfully phosphonylated through this procedure with tolerance of a broad range of functional groups.
Co-reporter:Shengying Wu, Jun Tang, Jianwei Han, Dan Mao, Xin Liu, Xing Gao, Jianjun Yu, Limin Wang
Tetrahedron 2014 70(35) pp: 5986-5992
Publication Date(Web):
DOI:10.1016/j.tet.2014.05.085
Co-reporter:Xin Liu;Dan Mao;ShengYing Wu;JianJun Yu;Gang Hong;Qiao Zhao
Science China Chemistry 2014 Volume 57( Issue 8) pp:1132-1136
Publication Date(Web):2014 August
DOI:10.1007/s11426-014-5140-9
An efficient approach for the synthesis of N-arylated amides was developed via copper(II) triflate-catalyzed direct oxidation of (aryl)methylamines to primary arylamides by air and subsequent N-arylation by diaryliodonium salts. Various substituted benzylamines could be applied in the reaction, providing a series of N-arylated amides in moderate to good yields. This method showed convenient, practical, and environment friendly advantages.
Co-reporter:An-yin Wang, Biao Chen, Lei Fang, Jian-jun Yu, Li-min Wang
Electrochimica Acta 2013 Volume 108() pp:698-706
Publication Date(Web):1 October 2013
DOI:10.1016/j.electacta.2013.07.017
A family of branched quaternary ammonium surfactants (compounds 1a–1c) with different carbon chains were synthesized for levelers applied in copper electroplating. Their inhibitory actions on copper electroplating were characterized by cyclic voltammetry (CV). Compound 1b, as representative structure type, was tested by means of different electrochemical methods including CV, polarization curve and electrochemical impedance spectroscopy (EIS) with different concentrations. The interaction between compound 1b and copper surface was investigated using atomic force microscope (AFM) and X-ray photoelectron spectra (XPS). The results indicated that our newly synthesized compounds, particular 1b, were effective levelers used for copper electroplating. Compound 1b could adsorb on copper surface to form an adsorption layer. The adsorption behavior of compound 1b on copper surface indicated that compound 1b could inhibit the copper electrodeposition, which provided favorable conditions used as a leveler. Moreover, the addition of compound 1b could increase the cathodic polarization, which was attributed to the adsorption of compound 1b during copper electroplating process. In addition, various surface morphologies and crystalline orientation of the plated copper films caused by different concentrations of compound 1b were characterized by scanning electron microscope (SEM) and X-ray diffraction (XRD) respectively. Effects of compound 1b on refining the grain size and changing the preferential orientation of the plated copper films were exhibited.
Co-reporter:Guanjun Zhang, Limin Wang, Xiaofei Cai, Liang Zhang, Jianjun Yu, Aili Wang
Dyes and Pigments 2013 Volume 98(Issue 2) pp:232-237
Publication Date(Web):August 2013
DOI:10.1016/j.dyepig.2013.02.015
•A novel diketopyrrolopyrrole (DPP) derivative was synthesized under mild conditions.•It was a fluorescent probe for fluoride ion with high sensitivity and selectivity.•The recognition mechanism was attributed to unique fluoride–boron interaction.•It could play an important role in the synthesis of organic optoelectronic materials.A new diketopyrrolopyrrole (DPP) derivative bearing pinacol boronate group has been synthesized via Suzuki–Miyaura reaction under mild conditions in good yield. The product could act as a colorimetric and ratiometric fluorescent probe for fluoride ion with high sensitivity and selectivity. The recognition mechanism was attributed to unique fluoride–boron interaction, which blocked the charge transfer (CT) between DPP chromophore and the empty p orbitals of boron atoms, and proved by the fluorescence spectra, 19F NMR spectra and 1H NMR spectra titration experiments.
Co-reporter:Guanjun Zhang, Shiming Bi, Longfeng Song, Feng Wang, Jianjun Yu, Limin Wang
Dyes and Pigments 2013 Volume 99(Issue 3) pp:779-786
Publication Date(Web):December 2013
DOI:10.1016/j.dyepig.2013.06.027
•We developed a new “turn on” fluorescent chemosensor DPPL2 for Zn2+.•It showed photoinduced electron transfer and intramolecular charge transfer effects.•This was the first DPP-based fluorescent chemosensor for heavy metal ions.•We provided an effective platform for developing new fluorescent probes.New turn-on fluorescent probe DPPL2, was rationally designed and synthesized based on the skeleton of diketopyrrolopyrrole (DPP), which presented sensitivity, selectivity for Zn2+ over other metal ions except some disturbance with Cd2+. Particularly, results demonstrated fluorescence enhancement and blue shift of DPPL2 upon Zn2+ binding. This phenomenon was a typical photoinduced electron transfer (PET) and intramolecular charge transfer (ICT) process which was attributed to diminishing the electron of the nitrogen lone pair delocalization on the DPP core upon Zn2+ binding. For comparison, DPPL3 (acylation of nitrogen atom of DPPL2) was synthesized and no fluorescence enhancement was observed, which further indicated that lone pair electrons of nitrogen atoms attached to DPP core were ascribed to PET process. 1H NMR titrations and DFT calculations also proved that PET and ICT process of system.
Co-reporter:Guanjun Zhang, Haiying Li, Shiming Bi, Longfeng Song, Yunxiang Lu, Liang Zhang, Jianjun Yu and Limin Wang
Analyst 2013 vol. 138(Issue 20) pp:6163-6170
Publication Date(Web):29 Jul 2013
DOI:10.1039/C3AN00873H
A new turn-on fluorescent chemosensor, DPPL1, was rationally designed and synthesized based on diketopyrrolopyrrole (DPP), which presented high sensitivity and selectivity for Zn2+. Specifically, DPPL1 presented a large emission enhancement and a 70 nm blue-shift upon Zn2+ binding. 1H NMR titrations, studies into the pH effects and DFT calculations further proved that this phenomenon was due to both photo-induced electron transfer (PET) and intra-molecular charge transfer (ICT) processes. More importantly, DPPL1 was successfully used for imaging Zn2+ in living HeLa cells. To the best of our knowledge, this is the first DPP-based fluorescent chemosensor to recognize Zn2+ ions in living cells with a large blue-shift and a fluorescent enhancement based on both photo-induced electron-transfer (PET) and intramolecular charge-transfer (ICT) effects. Meanwhile, we have also provided a new effective platform for the development of fluorescent chemosensors for other analytes.
Co-reporter:Fenglou Guo, Jianwei Han, Song Mao, Juan Li, Xu Geng, Jianjun Yu and Limin Wang
RSC Advances 2013 vol. 3(Issue 18) pp:6267-6270
Publication Date(Web):27 Feb 2013
DOI:10.1039/C3RA40374B
A novel approach towards the Pd-catalyzed arylation of electron-deficient polyfluoroarenes with diaryliodonium salts was developed. The desired fluorinated biaryls were synthesized in good yields. The mechanistic insights involving the PdII/IV catalytic cycle for the present reaction were discussed, which will be helpful in the understanding of catalytic arylations with diaryliodonium salts.
Co-reporter:Zhaoyu Fan, Matthieu Corbet, Yan Zhao, Floryan De Campo, Jean-Marc Clacens, Marc Pera-Titus, Pascal Métivier, Limin Wang
Tetrahedron Letters 2013 Volume 54(Issue 28) pp:3595-3598
Publication Date(Web):10 July 2013
DOI:10.1016/j.tetlet.2013.04.068
In the frame of biomass valorization, a novel and simple cyclic glyceryl sulfate was efficiently prepared in two steps from glycerol. It was shown to react efficiently with primary, secondary as well as tertiary amines to afford either the corresponding anionic or zwitterionic surface-active agents.Figure optionsDownload full-size imageDownload as PowerPoint slide
Co-reporter:Liang Zhang, Yefeng Wang, Jianjun Yu, Guanjun Zhang, Xiaofei Cai, Yue Wu, Limin Wang
Tetrahedron Letters 2013 Volume 54(Issue 31) pp:4019-4022
Publication Date(Web):31 July 2013
DOI:10.1016/j.tetlet.2013.05.076
A novel colorimetric and fluorescent sensor for Pd2+ has been developed based on the Pd-catalyzed deallylation. The sensor displays a highly sensitive and selective response with significant changes in both color (from orange to blue) and fluorescence (quenching).Figure optionsDownload full-size imageDownload as PowerPoint slide
Co-reporter:Shengying Wu;Limin Wang;Jun Tang;Dan Mao
Monatshefte für Chemie - Chemical Monthly 2013 Volume 144( Issue 3) pp:381-386
Publication Date(Web):2013 March
DOI:10.1007/s00706-012-0821-6
The stable and commercially available catalyst (1R,2R)-(+)-1,2-cyclohexanediamine l-tartrate complex was used for asymmetric aldol reaction in high yields (up to 99 %) and enantioselectivities [up to 94 % enantiomeric excess (ee)]. The catalyst was obtained easily and reused three times.
Co-reporter:Dan Mao, Jun Tang, Wenbo Wang, Shengying Wu, Xin Liu, Jianjun Yu, and Limin Wang
The Journal of Organic Chemistry 2013 Volume 78(Issue 24) pp:12848-12854
Publication Date(Web):December 4, 2013
DOI:10.1021/jo402331t
An unexpected cascade reaction of 2-aminobenzaldehydes with arylamines catalyzed by scandium pentafluorobenzoate [Sc(Pfb)3] was reported as a facile strategy for the efficient synthesis of a novel class of polycyclic ring-fused aminals N-substituted-6,7,11b,13-tetrahydro-6,12-[1,2]benzenoquinazolino[3,4-a]quinazolin-13-amines 1. Under similar conditions, a series of the analogues of Tröger’s base, 13-substituted-5,6,11,12-tetrahydro-6,12-epiminodibenzo[b,f][1,5]diazocines 2 were obtained when the arylamines were replaced by methanamines. A possible mechanism for the formation of 1 and 2 was proposed.
Co-reporter:Zhijun Chen, Limin Wang, Gang Zou, Xiaoming Cao, Yue Wu, Peijun Hu
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2013 Volume 114() pp:323-329
Publication Date(Web):October 2013
DOI:10.1016/j.saa.2013.05.072
•The fluorescence change occurs via reversible formation-separation of complex.•The sensor had a high selectivity for H2PO4-.•DFT calculations were used to verify the configuration of complex.A novel selective fluorescent chemosensor based on naphthalimide derivatives (AN-SB) was synthesized and characterized. Once combined with Cu2+, compound AN-SB could give rise to a visible yellow to orange color change and fluorescence quenching, while other metal ions showed subtle disturbance. The complex (AN-SB–Cu2+) formed by Cu2+ and AN-SB displayed high specificity for H2PO4-. Among the various anions, only H2PO4- induced the revival of color and fluorescence of AN-SB, resulting in “off–on” type sensing of H2PO4- anion. The signal transduction occured via reversible formation–separation of complex AN-SB–Cu2+, however, slight changes were observed in the presence of other anions.
Co-reporter:Zhijun Chen, Limin Wang, Gang Zou, Jun Tang, Xiaofei Cai, Mingshuang Teng, Li Chen
Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 2013 Volume 105() pp:57-61
Publication Date(Web):15 March 2013
DOI:10.1016/j.saa.2012.12.005
A new fluorescent probe, DN-SB, was synthesized. DN-SB was based on the naphthalimide derivatives and exhibited high selectivity and sensitivity for Cu2+ ions. As a Cu2+-amplified fluorescent probe, its fluorescence spectrum showed 4.5-fold enhancement in the intensity of the signal at 519 nm on binding with the Cu2+. Based on the fluorescence titration spectra and job’s-plot, binding mode of DN-SB with Cu2+ was proposed. Fluorescence intensity was linear with concentration of Cu2+ cation in a range from 4 μM to 7 μM. DN-SB was also sensitive for copper ions. The detection limit was calculated to be 0.15 μM which indicated DN-SB was sensitive to Cu2+.Graphical abstractHighlights► It was a turn-on sensor for copper(II) ions based on naphthalimide derivatives. ► It had a good selectivity for copper(II) ions. ► The sensor had a low detection limit (0.15 μM).
Co-reporter:Lei Fang, Jianjun Yu, Ying Liu, Anyin Wang, Limin Wang
Tetrahedron 2013 69(51) pp: 11004-11009
Publication Date(Web):
DOI:10.1016/j.tet.2013.10.029
Co-reporter:Zhi Jun Chen, Li Min Wang, Gang Zou, Liang Zhang, Guan Jun Zhang, Xiao Fei Cai, Ming Shuang Teng
Dyes and Pigments 2012 Volume 94(Issue 3) pp:410-415
Publication Date(Web):September 2012
DOI:10.1016/j.dyepig.2012.01.024
Based on a perylene diimide derivatives(PDIs) platform, AM-PDIs was rationally designed and synthesized as a new colorimetric and ratiometric fluorescent sensor for naked-eye detection of fluoride ion with high selectivity over other halide ions. Addition of fluoride ion to a dichloromethane(DCM) solution of AM-PDIs resulted in an obvious color change (from red to blackish green) because of a large red shift (151 nm) in absorption. The recognition mechanism was attributed to the intermolecular proton transfer between a hydrogen atom on the amide N position of sensor and the fluoride anion. The detection limit was calculated to be 0.14 μM.Highlights► It was the first time to report ratiometric chemsensor for F anion based on PDIs. ► This sensor showed a large red shift(151 nm) in absorption. ► The sensor had a low detection limit(0.14 μM).
Co-reporter:Yilin Sun, Guangming Wu, Dinghai Cen, Yaofeng Chen and Limin Wang
Dalton Transactions 2012 vol. 41(Issue 32) pp:9682-9688
Publication Date(Web):11 Jun 2012
DOI:10.1039/C2DT30763D
Four multitopic Schiff-base ligand precursors were synthesized via condensation of 4,4′-diol-3,3′-diformyl-1,1′-diphenyl or 1,3,5-tris(4-hydroxy-5-formylphenyl)benzene with 2,6-diisopropylaniline or 2,6-dimethylaniline. Amine elimination reactions of Ln[N(SiMe3)2]3 (Ln = La, Nd, Sm or Y) with these multitopic ligand precursors gave ten heterogeneous rare-earth metal catalysts. These heterogeneous rare-earth metal catalysts are active for intramolecular hydroalkoxylation of alkynols, and the catalytic activities are influenced by the ligand and metal ion. The recycling experiment on the most active heterogeneous catalyst showed the catalyst has a good reusability.
Co-reporter:Fenglou Guo;Dr. Limin Wang;Peiqi Wang;Dr. Jianjun Yu;Dr. Jianwei Han
Asian Journal of Organic Chemistry 2012 Volume 1( Issue 3) pp:218-221
Publication Date(Web):
DOI:10.1002/ajoc.201200071
Co-reporter:Jinqian Liu, Limin Wang, Xingzhou Zheng, Aili Wang, Mengyun Zhu, Jianjun Yu, Qiang Shen
Tetrahedron Letters 2012 Volume 53(Issue 14) pp:1843-1846
Publication Date(Web):4 April 2012
DOI:10.1016/j.tetlet.2012.01.141
A simple, inexpensive, environmentally friendly, and highly efficient benzylation and allylation of 1,3-dicarbonyl compounds with sulfonamides in the presence of Yb(OTf)3 is described. Yb(OTf)3 was proved to be a good catalyst for the cleavage of sp3 carbon–nitrogen bond. Various 1,3-dicarbonyl compounds can couple with a broad range of tosyl-activated benzylic and allylic amines to give diversely functionalized products in good to excellent yields.
Co-reporter:Liang Zhang;Limin Wang;Guanjun Zhang;Jianjun Yu;Xiaofei Cai;Mingshuang Teng ;Yue Wu
Chinese Journal of Chemistry 2012 Volume 30( Issue 12) pp:2823-2826
Publication Date(Web):
DOI:10.1002/cjoc.201201116
Abstract
A novel colorimetric chemosensor PBIOSi has been designed and synthesized. The addition of F− to a THF solution of PBIOSi resulted in an obvious color change (from red to green) in a short time because of the specific cleavage of SiO bond in PBIOSi by F−. It was interesting that PBIOSi showed excellent selectivity for F− detection over other halides. The UV-Vis absorption and fluorescence were changed linearly with the concentration of F− over the range of 0–10 µmol/L.
Co-reporter:Zhijun Chen;Limin Wang;Gang Zou;Mingshuang Teng;Jianjun Yu
Chinese Journal of Chemistry 2012 Volume 30( Issue 12) pp:2844-2848
Publication Date(Web):
DOI:10.1002/cjoc.201201070
Abstract
A new fluorescent probe, NPQ-C, was synthesized. NPQ-C was based on the naphthalimide derivatives and exhibited high selectivity and sensitivity for Cr3+ ions. As a Cr3+-amplified fluorescent probe, Its fluorescence spectrum showed 5.5-fold enhancement in the intensity of the signal at 500 nm on binding with the Cr3+. Based on the fluorescence titration spectra and Job's-plot analysis, binding mode of NPQ-C with Cr3+ was proposed. Fluorescence intensity was linear with concentration of Cr3+ cation in a range from 0 to 10 µmol·L−1. NPQ-C was also sensitive for Cr3+. The detection limit was calculated to be 0.20 µmol·L−1 which indicated that NPQ-C was sensitive to Cr3+.
Co-reporter:Jianjun Yu;Limin Wang;Mingtao Liu;Jun Qiu;Qiang Shen;Lei Fang ;Jun Tang
Chinese Journal of Chemistry 2012 Volume 30( Issue 5) pp:1114-1118
Publication Date(Web):
DOI:10.1002/cjoc.201100544
Abstract
A novel PdCl2/bis(2-pyridylmethyl)amine-based ligand (1) catalytic system, which is water-soluble and air-stable, has been successfully synthesized and applied for Suzuki-Miyaura cross-coupling reaction. In the presence of catalytic amount of PdCl2/1 system, arylboronic acids can couple with a wide range of aryl halides, including aryl bromides and aryl chlorides. The reactions proceed under mild conditions to give excellent yields, and a wide range of functionalities is tolerated.
Co-reporter:Fenglou Guo, Limin Wang, Song Mao, Chi Zhang, Jianjun Yu, Jianwei Han
Tetrahedron 2012 68(39) pp: 8367-8370
Publication Date(Web):
DOI:10.1016/j.tet.2012.06.107
Co-reporter:Jun Qiu, Limin Wang, Mingtao Liu, Qiang Shen, Jun Tang
Tetrahedron Letters 2011 Volume 52(Issue 48) pp:6489-6491
Publication Date(Web):30 November 2011
DOI:10.1016/j.tetlet.2011.09.115
A highly efficient, convenient, and environmentally friendly protocol was developed for the PdCl2-catalyzed ligandless and additive-free Suzuki reaction of aryl bromides with arylboronic acids in water/ethanol.
Co-reporter:Jun Tang, Limin Wang, Yinfang Yao, Liang Zhang, Wenbo Wang
Tetrahedron Letters 2011 Volume 52(Issue 4) pp:509-511
Publication Date(Web):26 January 2011
DOI:10.1016/j.tetlet.2010.11.102
A family of 2-amino-3-cyanopyridine derivatives are synthesized from aldehydes, ketones, malononitrile, and ammonium acetate via one-pot reaction catalyzed by ytterbium perfluorooctanoate [Yb(PFO)3]. This procedure tolerates most of substrates and has the advantages of short routine, high yields, and environmentally friendly. Furthermore, the possible mechanism is also proposed.
Co-reporter:Jun Tang, Limin Wang, Wenbo Wang, Liang Zhang, Shengying Wu, Dan Mao
Journal of Fluorine Chemistry 2011 Volume 132(Issue 2) pp:102-106
Publication Date(Web):February 2011
DOI:10.1016/j.jfluchem.2010.12.002
Three-component reactions of aldehydes, amines and diethyl phosphite are efficiently catalyzed by ytterbium perfluorooctanoate [Yb(PFO)3] under solvent-free conditions, giving the corresponding α-aminophosphonates in good to excellent yields. The catalyst can be recovered and reused for several times without any significant loss of activity. Furthermore, a possible mechanism for this transformation is also presented.Graphical abstractAn efficient and one-pot protocol for the synthesis of α-aminophosphonates promoting by ytterbium perfluorooctanoate [Yb(PFO)3] under solvent-free conditions is described.Research highlights▶ α-Aminophosphonates are synthesized from one-pot reactions. ▶ The reactions are promoted efficiently by ytterbium perfluorooctanoate. ▶ The reactions are undergoing in solvent-free conditions. ▶ The catalyst can be recycled and reused. ▶ The methodology tolerates most of substrates.
Co-reporter:Jun Tang, Limin Wang, Dan Mao, Wenbo Wang, Liang Zhang, Shengying Wu, Yongshu Xie
Tetrahedron 2011 67(44) pp: 8465-8469
Publication Date(Web):
DOI:10.1016/j.tet.2011.09.004
Co-reporter:Jian-Jun Yu, Li-Min Wang, Jin-Qian Liu, Feng-Lou Guo, Ying Liu and Ning Jiao
Green Chemistry 2010 vol. 12(Issue 2) pp:216-219
Publication Date(Web):09 Dec 2009
DOI:10.1039/B913816A
A simple, environmentally friendly, tandem Knoevenagel condensation and Michael addition procedure is reported. The reactions between cyclic-13-diketones and a variety of aldehydes were carried out in water to afford tetraketones (64–99%). In this green synthetic protocol, the solvent water itself catalysed the reaction by hydrogen bonding, thus avoiding the use of any other catalysts to make the work up procedure easier.
Co-reporter:Ying Liu; Dr. Limin Wang;Yuanyuan Sui ;Jianjun Yu
Chinese Journal of Chemistry 2010 Volume 28( Issue 10) pp:2039-2044
Publication Date(Web):
DOI:10.1002/cjoc.201090340
Abstract
By using solvent-free and heat conditions, the Petasis boronic Mannich reaction of salicylaldehydes with various boronic acids and secondary amines without catalyst is described. The alkylaminophenols were obtained in moderate to good yields in a shorter reaction time than the traditional methods.
Co-reporter:Wei Shen;Limin Wang;Jun Tang;Zhenhua Qian ;Xiaofeng Tong
Chinese Journal of Chemistry 2010 Volume 28( Issue 3) pp:443-448
Publication Date(Web):
DOI:10.1002/cjoc.201090094
Abstract
The Michael addition of indoles to electron-deficient nitroolefins was effectively catalyzed by an ionic liquid-coordinated ytterbium(III) sulfonate catalyst. The recycling procedure of the catalyst was very simple without extraction with water, and the catalyst was reused for five times without any loss of its catalytic activity. Furthermore, to demonstrate the application of this methodology, the Pictet-Spengler reaction was chosen and successfully carried out in the mixture of Br?nsted-acidic ionic liquid and [bmim]BF4.
Co-reporter:Li-Min Wang, Ning Jiao, Jun Qiu, Jian-Jun Yu, Jin-Qian Liu, Feng-Lou Guo, Ying Liu
Tetrahedron 2010 66(1) pp: 339-343
Publication Date(Web):
DOI:10.1016/j.tet.2009.10.091
Co-reporter:Limin WANG;Yinfang YAO;Yonghong WANG;Gang ZOU
Chinese Journal of Chemistry 2009 Volume 27( Issue 2) pp:343-346
Publication Date(Web):
DOI:10.1002/cjoc.200990055
Abstract
A CMC-supported lanthanide catalyst was prepared from CMC and isopropoxy lanthanide. This solid Lewis acid catalyst was used in synthesis of substituted imidazoles under mild conditions, showing catalytic activity comparable to the expensive lanthanide Lewis acid Ln(OTf)3. Furthermore, the catalyst could be readily recycled and reused for five times without any appreciable loss in catalytic activity.
Co-reporter:Li-Min Wang, Liang Hu, Hong-Juan Chen, Yuan-Yuan Sui, Wei Shen
Journal of Fluorine Chemistry 2009 Volume 130(Issue 4) pp:406-409
Publication Date(Web):April 2009
DOI:10.1016/j.jfluchem.2009.01.002
Ytterbium perfluorooctanoate [Yb(PFO)3] has been proved to be an efficient catalyst for Doebner reaction of pyruvic acid, aldehydes and amines under mild conditions in water to afford quinoline-4-caboxylic acid derivatives with three component one-pot method in good yields. The process is operationally simple and environmentally benign and the catalyst has readily been recycled for several times with consistent activity. Furthermore, a plausible mechanism for this transformation is also presented.Ytterbium perfluorooctanoate [Yb(PFO)3] catalyzed efficient Doebner reaction through three component coupling reactions of pyruvic acid, amines and aldehydes in water was described as a novel procedure for the preparation of quinoline-4-carboxylic acid derivatives.
Co-reporter:Wei Shen, Li-Min Wang, He Tian, Jun Tang, Jian-jun Yu
Journal of Fluorine Chemistry 2009 Volume 130(Issue 6) pp:522-527
Publication Date(Web):June 2009
DOI:10.1016/j.jfluchem.2009.02.014
One-pot three-component synthesis of 1,8-dioxo-9,10-diaryl-decahydroacridines in water was efficiently realized in the presence of the Brønsted acidic imidazolium salts containing perfluoroalkyl tails in good yields. The method provided several advantages such as low catalyst loading; recycle of the catalyst and simple work procedure.A simple and one-pot protocol for the synthesis of 1,8-dioxo-9,10-diaryl-decahydroacridines via Brønsted acidic imidazolium salts containing perfluoroalkyl tails catalyzed three-component reactions in water has been described.
Co-reporter:Jie Wu, Li-Min Wang, Ping Zhao, Feng Wang, Guifeng Wang
Progress in Organic Coatings 2008 Volume 63(Issue 2) pp:189-194
Publication Date(Web):September 2008
DOI:10.1016/j.porgcoat.2008.05.008
C.I. pigment red 170 is an important type of organic pigment. A new type of quaternary ammonium salt containing siloxane group was prepared and then used as a favorable dispersant in the surface treatment of pigment red 170. The quaternary ammonium salt was achieved from the reaction of N-(β-aminoethyl)-γ-aminopropyl-methyl-bimethoxy-silane and 3-chloro-2-hydroxypropyl-bimethyl-hexadecyl ammonium halide in isopropanol, and its structure was characterized by IR and NMR techniques. The flowability, dispersing extent, particle size, and wetting behaviors of pigment were determined and the results showed that a small amount of the above dispersant could bring to the high flowability, good dispersing stability, small particle size and excellent wettability of pigment red 170. We also proposed the scenarios of dispersing process of pigment red 170 based on the information obtained from above characterizations.
Co-reporter:Li-Min WANG;Yuan-Yuan SUI ;Liang ZHANG
Chinese Journal of Chemistry 2008 Volume 26( Issue 6) pp:1105-1108
Publication Date(Web):
DOI:10.1002/cjoc.200890196
Abstract
A series of 14-{[(Un)substituted phenyl] or alkyl}-14H-dibenzo[a,j]xanthenes were prepared under solvent-free conditions by Yb(OTf)3 catalyzed condensation reactions of β-naphthol with various aldehydes. The process presented here is operationally simple, environmentally benign and has good to excellent yields. Furthermore, the catalyst can be recovered conveniently and reused efficiently.
Co-reporter:Wei Shen, Li-Min Wang, He Tian
Journal of Fluorine Chemistry 2008 Volume 129(Issue 4) pp:267-273
Publication Date(Web):April 2008
DOI:10.1016/j.jfluchem.2007.12.002
A newly prepared quaternary ammonium salt (QAS) gemini fluorosurfactants efficiently catalyze one-pot Mannich reactions of aldehydes, amines and ketones in aqueous media at ambient temperature to afford corresponding β-aminocarbonyl compounds in good to excellent yields. In addition, the gemini fluorosurfactant catalysts were recovered and reused for three times with little loss of their catalytic activities.A new perfluorooctylated quaternary ammonium salt (QAS) gemini surfactant was synthesized and used as organic catalyst to promote Mannich reactions in water at room temperature successfully.
Co-reporter:Li-Min Wang;Liang Zhang;Liang Hu;He Tian
Chinese Journal of Chemistry 2007 Volume 25(Issue 3) pp:
Publication Date(Web):5 MAR 2007
DOI:10.1002/cjoc.200790071
An efficient method has been developed for one-pot three-component coupling reactions of various aldehydes, 1-cyclohexen-2-one, and primary or secondary amines in the presence of a catalytic amount of Yb(OTf)3 under mild conditions to afford the corresponding 2-arylmethyl N-substituted anilines in good yields. In addition, the catalyst was easily recovered and could be reused for at least four cycles without any loss of activity.
Co-reporter:Li-Min Wang, Jue-Hua Shao, He Tian, Yong-Hong Wang, Bo Liu
Journal of Fluorine Chemistry 2006 Volume 127(Issue 1) pp:97-100
Publication Date(Web):January 2006
DOI:10.1016/j.jfluchem.2005.10.004
Rare earth perfluorooctanoate [RE(PFO)3] catalyzes facile condensation of dimedone, aldehydes and malononitrile under mild conditions to afford the corresponding 5-oxo-5,6,7,8-tetrahydro-4H-benzo-[b]-pyran derivatives in good to high yields. The catalyst can be easy to prepare, stable and storable, easily recycled and reused for several cycles with consistent activity.In this article, we have used Yb(PFO)3 as a new and effective catalyst in one-pot reaction of synthesis of benzopyran derivatives under mild condition with good to excellent yields.
Co-reporter:Limin Wang;Jijun Liu;He Tian;Changtao Qian;Jie Sun
Advanced Synthesis & Catalysis 2005 Volume 347(Issue 5) pp:
Publication Date(Web):8 APR 2005
DOI:10.1002/adsc.200404211
Ytterbium(III) triflate efficiently catalyzes the one-pot reaction of homophthalic anhydride with aldehydes and amines at ambient temperature to afford the corresponding cis-isoquinolonic acid derivatives in good to excellent yields with high diastereoselectivity. This method provides a novel and much improved modification of the three-component reaction in terms of mild reaction conditions, short reaction times, clean reaction profiles, small quantity of catalyst, and simple work-up procedure. Another important feature of this method is that the catalyst can be easily recovered from the aqueous layer after the reaction and can be reused with no loss of activity.
Co-reporter:Shiming Bi, Guanjun Zhang, Yue Wu, Shengying Wu, Limin Wang
Dyes and Pigments (November 2016) Volume 134() pp:586-592
Publication Date(Web):November 2016
DOI:10.1016/j.dyepig.2016.08.001
Co-reporter:Xing Gao, Jianwei Han and Limin Wang
Inorganic Chemistry Frontiers 2016 - vol. 3(Issue 6) pp:
Publication Date(Web):
DOI:10.1039/C6QO00074F
Co-reporter:Dan Mao, Jun Tang, Wenbo Wang, Xin Liu, Shengying Wu, Jianjun Yu and Limin Wang
Organic & Biomolecular Chemistry 2015 - vol. 13(Issue 7) pp:NaN2128-2128
Publication Date(Web):2014/12/03
DOI:10.1039/C4OB02220C
An unexpected Sc(OTf)3-catalyzed and air-mediated cascade reaction of o-aminoacetophenones with methanamines was discovered as an efficient synthetic approach to a novel class of fluorescent fused-four-ring dibenzo[b,h][1,6]naphthyridine derivatives. Two possible mechanisms of the reaction were proposed. The photophysical properties of the dibenzo[b,h][1,6]naphthyridine 1a were initially considered.
Co-reporter:Yilin Sun, Guangming Wu, Dinghai Cen, Yaofeng Chen and Limin Wang
Dalton Transactions 2012 - vol. 41(Issue 32) pp:NaN9688-9688
Publication Date(Web):2012/06/11
DOI:10.1039/C2DT30763D
Four multitopic Schiff-base ligand precursors were synthesized via condensation of 4,4′-diol-3,3′-diformyl-1,1′-diphenyl or 1,3,5-tris(4-hydroxy-5-formylphenyl)benzene with 2,6-diisopropylaniline or 2,6-dimethylaniline. Amine elimination reactions of Ln[N(SiMe3)2]3 (Ln = La, Nd, Sm or Y) with these multitopic ligand precursors gave ten heterogeneous rare-earth metal catalysts. These heterogeneous rare-earth metal catalysts are active for intramolecular hydroalkoxylation of alkynols, and the catalytic activities are influenced by the ligand and metal ion. The recycling experiment on the most active heterogeneous catalyst showed the catalyst has a good reusability.
Co-reporter:Yankai Li, Shiming Bi, Fei Liu, Shengying Wu, Jun Hu, Limin Wang, Honglai Liu and Ying Hu
Journal of Materials Chemistry A 2015 - vol. 3(Issue 26) pp:NaN6881-6881
Publication Date(Web):2015/05/26
DOI:10.1039/C5TC00682A
Most organic dyes dissipate their excitation energy in the aggregated state because of the “aggregation-caused quenching” effect, deteriorating their application in optoelectronic devices. To prevent the “aggregation-caused quenching” effect, we incorporate a dye-based fluorophore into a porous organic polymer skeleton because porosity would allow the spatial isolation of fluorophores to maintain their emission. Tuning the fraction of fluorophores in the skeleton of FL-SNW-DPPs could spread the emission color coverage from red to blue in both solid-state and suspension. More importantly, the combination of fluorescence and porosity of FL-SNW-DPPs would provide more space to transduce the molecular interaction between adsorbed analytes and fluorophores to the detectable changes in light emission, leading to the fluorescence-off or fluorescence-on detection of electron-deficient or electron-rich analytes.
Co-reporter:Chen Hu, Gang Hong, Xiaofei Qian, Kwang Rim Kim, Xiaoyan Zhu and Limin Wang
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 23) pp:NaN4991-4991
Publication Date(Web):2017/05/18
DOI:10.1039/C7OB01025G
A new cross-coupling reaction of N-benzylic sulfonamides with 2-substituted cyanoacetates for the synthesis of 2-substituted benzylbenzene was reported. In the presence of AlCl3, a broad range of N-benzylic sulfonamides reacted smoothly with 2-substituted cyanoacetates to afford structurally diverse benzylbenzenes in moderate to excellent yields. The conversion could be enlarged to gram-scale efficiently. The practicability of this approach was further manifested in the synthesis of a related bioactive agent with high anti-inflammatory activity.
Co-reporter:Xinjin Li, Jingwei Zhao, Mingyou Hu, Dingben Chen, Chuanfa Ni, Limin Wang and Jinbo Hu
Chemical Communications 2016 - vol. 52(Issue 18) pp:NaN3660-3660
Publication Date(Web):2016/02/01
DOI:10.1039/C5CC10550A
A new method for the generation of the “PhSO2CF2Cu” species from readily available difluoromethyl phenyl sulfone (PhSO2CF2H) has been developed. The “PhSO2CF2Cu” reagent can be applied in (phenylsulfonyl)difluoromethylation of arylboronic acids, which affords a convenient approach to introducing the PhSO2CF2 group into aromatics.