Jianhui Wang

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Name: 王建辉
Organization: Tianjin University , China
Department: Department of Chemistry
Title: Professor(PhD)

TOPICS

Co-reporter:Mengwei Li;Yi-Xuan Wang;Yulan Chen
Journal of Materials Chemistry C 2017 vol. 5(Issue 13) pp:3408-3414
Publication Date(Web):2017/03/30
DOI:10.1039/C7TC00173H
A facile approach to synthesize stereospecific (Z)-aryl-functionalized 1,4-enediones has been presented. The resulting molecules (TPBD-1 and TPBD-2) were demonstrated as a new type of heteroatom-containing AIE-active luminogens with multiple sites for structural modifications. Knoevenagel reaction of TPBD-1 led to a high electron affinity cyano derivative (TPBD-CN), which showed enhanced AIE performance and pronounced red-emission. More interestingly, TPBD-1 exhibited acid-induced red emission both in dilute solution and in the solid state, which is attractive due to its great potential for turn-on optical sensing. The reversible fluorescence acid sensing can be attributed to the stepwise binding effect of carbonyl groups on the 1,4-enedione core to rigidify the molecular conformation and strengthen the D–A interaction, which was systematically investigated by UV-vis, FL, FT-IR, and NMR spectroscopy and was further corroborated by DFT calculations.
Co-reporter:Weijie Guo;Maocong Yi;Guiyan Liu
Chinese Journal of Chemistry 2017 Volume 35(Issue 10) pp:1569-1574
Publication Date(Web):2017/10/01
DOI:10.1002/cjoc.201700150
An atom economical highly efficient method has been developed for the synthesis of quinoline and 1,2,3,4-tetrahydroquinoline derivatives from o-nitrotoluenes bearing electron-withdrawing groups and olefins (acrylic esters, acrylonitriles, and methyl acrylates) via a base-catalyzed [2 + 4] cycloaddition. This simple, rapid, and environment- friendly method provides a practical pathway for the synthesis of quinoline and 1,2,3,4-tetrahydroquinoline derivatives. The starting materials are readily available and 37 products were obtained in good to excellent yields.
Co-reporter:Xiaobo Yu, Ligai Zhang, Xiaomei Han, Jianhui Wang, Yun Tian, Guiyan Liu
Journal of Organometallic Chemistry 2017 Volume 833(Volume 833) pp:
Publication Date(Web):15 March 2017
DOI:10.1016/j.jorganchem.2017.01.022
•A new synthetic method for the preparation of diphenoquinone derivates has been developed.•The diphenoquinone derivates are synthesized via the triphenylboron induced radical coupling of lithium o-lithio-phenolate.•A mechanism including the in situ initiation of a free radical coupling process through triphenylborane is proposed.Organoborane have been recognized to participate in free-radical processes. Herein, the concept of using organoboranes as a radical initiator has been extended to aromatic compounds. Organoborane promoted in situ coupling reaction of phenolate was observed during its reaction with dilithium phenolate, leading to a new synthetic method for the preparation of diphenoquinone derivates in medium to good yields.Download high-res image (106KB)Download full-size image
Co-reporter:Yulian Duan;Tao Wang;Qingxiao Xie;Xiaobo Yu;Weijie Guo;Shutao Wu;Danfeng Li;Guiyan Liu
Dalton Transactions 2017 vol. 46(Issue 18) pp:5986-5993
Publication Date(Web):2017/05/09
DOI:10.1039/C7DT00853H
An indolinooxazolidine tagged N-heterocyclic carbene Ru olefin metathesis catalyst was synthesized and the molecular structure of this new Ru complex was determined by single crystal X-ray diffraction. This complex is a homogeneous catalyst and can be recovered by controlling the polarity of the indolinooxazolidine tag. Under acidic conditions the indolinooxazolidine tag exists as an open protonated form and under basic conditions the tag is in a closed form. The distribution of this catalyst in a two-phase system can be controlled by simply changing the pH, making the recovery of this catalyst easily obtainable.
Co-reporter:Guiyan Liu, Chengxin Liu, Xia Zhao and Jianhui Wang  
RSC Advances 2016 vol. 6(Issue 50) pp:44475-44479
Publication Date(Web):29 Apr 2016
DOI:10.1039/C6RA08272F
The design and synthesis of a stable, highly active, and recyclable homogeneous palladium catalyst for Suzuki–Miyaura coupling reactions is of great interest. A well-defined N-heterocyclic carbene (NHC) Pd(II) complex with pH- and light-sensitive nitrobenzospiropyran (SP) tags has been synthesized in good yields via a series of simple steps. This complex is a homogeneous catalyst which has excellent reactivities for the Suzuki–Miyaura coupling of aryl bromides and aryl chlorides with arylboronic acids. Significantly, at a low loading (0.2 mol%), this catalyst has very good recyclability in an i-PrOH–H2O solvent system (1:1 v/v), under mild conditions. By making use of the pH- and light-sensitive SP tags, the catalyst can be recovered and reused seven times.
Co-reporter:Xiaobo Yu, Jingjing Wang, Weijie Guo, Yun Tian, and Jianhui Wang
Organometallics 2016 Volume 35(Issue 11) pp:1876-1884
Publication Date(Web):May 27, 2016
DOI:10.1021/acs.organomet.6b00238
Unsymmetrical biaryls were synthesized by oxidative coupling reactions between aromatic primary alcohols and arylboronic acids through the C–C bond cleavage of the primary alcohols chelated with a rhodium catalyst. The desired unsymmetrical biaryl products were obtained in good to excellent yields under the optimized reaction conditions. A wide variety of functionalities are compatible with the reaction under the optimized conditions. This new coupling strategy provides a favorable method to construct valuable biaryl compounds from aromatic primary alcohols which are cheap, environmentally friendly, and easily accessible substrates.
Co-reporter:Guiyan Liu, Maocong Yi, Lu Liu, Jingjing Wang and Jianhui Wang  
Chemical Communications 2015 vol. 51(Issue 14) pp:2911-2914
Publication Date(Web):17 Dec 2014
DOI:10.1039/C4CC09358E
A highly efficient one-pot procedure for the preparation of substituted quinolines from substituted o-nitrotoluenes with electron-withdrawing groups and olefins (acrylic esters and acrylonitriles) using a cesium catalyst has been developed. A plausible [2+4] cycloaddition mechanism is proposed. This method uses nitroaromatic compounds as the starting materials to give quinoline derivatives in good to high yields under mild conditions with no transition metal catalysis. It provides an atom economical pathway for the synthesis of quinoline derivatives which could be used in industrial processes.
Co-reporter:Xia Liu, Ze Yi, Maocong Yi, Jianhui Wang, Guiyan Liu
Tetrahedron 2015 Volume 71(Issue 28) pp:4635-4639
Publication Date(Web):8 July 2015
DOI:10.1016/j.tet.2015.05.008
A new rhodium-catalyzed cross-coupling of carboxylic acid anhydrides and potassium aryltrifluoroborates was described. In this system CuI played a very important role. Various functionalities were compatible in the reaction, and the desired products were obtained in good to excellent yields. A mechanism of this reaction using a Rh(I) model catalyst have also been proposed.
Co-reporter:Lu Liu;Fang Wang;Zhenghong Li ;Dr. Jianhui Wang
Asian Journal of Organic Chemistry 2014 Volume 3( Issue 6) pp:695-699
Publication Date(Web):
DOI:10.1002/ajoc.201402035

Abstract

A highly efficient method for the synthesis of fluorenones through a palladium-catalyzed intramolecular oxidative coupling reaction via dual CH activations is reported. In this reaction, substituted fluorenones were obtained in moderate to high yields from diphenylacetic acid and its derivatives as substrates. The carboxylate, as a removable directing group, plays an important role in the dual CH activations of the substrate. The current method provides an efficient synthetic route for producing a variety of substituted fluorenones under mild reaction conditions.

Co-reporter:Yiran Zhang, Mingbo Shao, Huizhu Zhang, Yuqing Li, Dongyu Liu, Yu Cheng, Guiyan Liu, Jianhui Wang
Journal of Organometallic Chemistry 2014 Volume 756() pp:1-9
Publication Date(Web):15 April 2014
DOI:10.1016/j.jorganchem.2014.01.017
•A series of new oxygen chelated ruthenium carbene metathesis catalysts containing carbonyl groups were presented.•Complex was characterized by X-ray, NMR and elemental analysis.•Catalytic study for ring-closing metathesis and cross metathesis was evaluated.•Highly activity for RCM of many substrates was showed.The rate of initiation of Hoveyda catalysts is affected by the electronic and steric effects that act upon the Ru⋯O coordination. In order to boost the activity of Hoveyda catalysts, a series of new oxygen chelated ruthenium carbene metathesis catalysts containing an N-heterocyclic carbene (NHC) and a carbonyl group has been developed, and their catalytic activities for olefin metathesis reactions were investigated. The aliphatic end groups of complexes (H2IMes)(Cl)2RuC(H)[(C6H3X)OCH(Me)(C(O)OEt)(X = H, OMe, Me, NO2)] were functionalized by the attachment of a straight-chain ester. The X-ray structures of complex (H2IMes)(Cl)2RuC(H)[(C6H4)OCH(Me)(C(O)NMe2)] showed that the carbonyl oxygen of the amide and the terminal oxygen of the benzylidene ether are both coordinated to the metal to give an octahedral structure. However, the carbonyl oxygen of complexes (H2IMes)(Cl)2RuC(H)[(C6H3X)OCH(CH2C(O)OCH2)(X = H, OMe)] does not coordinate to the metal due to the steric effect of the lactone. All these complexes were used as catalysts for olefin metathesis reactions and all exhibited excellent performances for the ring-closing metathesis (RCM) of diethyl diallymalonate at 30 °C. The initiation rate of these catalysts was higher than that for the Hoveyda catalyst ((H2IMes)(Cl)2RuC(H)(C6H4-2-OiPr)) and these complexes are also active for cross metathesis (CM).Oxygen chelated ruthenium carbene metathesis catalysts containing an N-heterocyclic carbene (NHC) and a carbonyl group.
Co-reporter:Guiyan Liu, Mingbo Shao, Huizhu Zhang, Jianhui Wang
Polyhedron 2014 Volume 76() pp:51-54
Publication Date(Web):7 July 2014
DOI:10.1016/j.poly.2014.03.034
New oxygen chelated ruthenium carbene complex containing carbonyl oxygen and ether oxygen has been developed. The X-ray structure of the complex showed that the carbonyl oxygen of the amide and the terminal oxygen of the benzylidene ether are both coordinated to the metal to give an octahedral structure. The catalytic activities of this new complex for olefin metathesis reactions were investigated and it exhibited excellent performances for the ring-closing metathesis (RCM) of diethyl diallymalonate at 30 °C and even at 0 °C. The initiation rate of the catalyst was higher than that for the Hoveyda catalyst ((H2IMes)(Cl)2Ru = C(H)(C6H4-2-OiPr)) and it was also active for cross metathesis (CM).Graphical abstractA new oxygen chelated ruthenium (II) carbene complex has been prepared and characterized. The structure of ruthenium (II) complex has been determined by X-ray crystallography. This complex was found to be efficient for the ring-closing metathesis reaction at 0 °C.
Co-reporter:Jingjing Wang, Sujing Zuo, Weiqiang Chen, Xinrui Zhang, Kaixin Tan, Yun Tian, and Jianhui Wang
The Journal of Organic Chemistry 2013 Volume 78(Issue 17) pp:8217-8231
Publication Date(Web):June 7, 2013
DOI:10.1021/jo400949p
A new method for building aryl aryl ketones containing heterocyclic rings through chelation-assisted C–O bond activation catalyzed by a rhodium complex has been developed. In this reaction, methyl quinoline-8-carboxylate, methyl quinoxaline-5-carboxylate, and their derivatives were reacted with an excess amount of a substituted phenyl boronic acid in the presence of a rhodium(I) complex to give substituted phenyl(quinolin-8-yl)methanone, phenylquinoxalin-5-ylmethanone, and their derivatives in medium to high yields. The current method offers a highly favorable synthetic pathway to efficiently build related drugs with an 8-benzoylquinoline core structure. This method may prove especially valuable for medicinal chemists for the late-stage introduction of versatile ketone moieties into complex scaffolds for diversity-oriented synthetic strategies.
Co-reporter:Xinrui Zhang, Jingjing Wang, Hui Zhao, Haitao Zhao, and Jianhui Wang
Organometallics 2013 Volume 32(Issue 12) pp:3529-3536
Publication Date(Web):June 13, 2013
DOI:10.1021/om4003736
A rhodium-catalyzed [6 + 2] cycloaddition of internal alkynes with cycloheptatriene is described. A series of substituted alkynes were cycloadded to cycloheptatriene through a [6 + 2] addition to give a variety of substituted bicyclic compounds in excellent yields. The optimal catalytic system for these transformations was a [Rh(COD)Cl]2 (5.0 mol %) catalyst in combination with CuI (10 mol %) and PPh3 (10 mol %). The proposed mechanism for this system includes an initial oxidative coupling reaction between the coordinated cycloheptatriene and the internal alkyne, followed by a [1,3]-shift of the Rh metal center and a reductive elimination from the Rh(III)–allyl complex to give the final product. Calculations using a model Rh(I) catalyst were also carried out to further understand this mechanism.
Co-reporter:Weiqiang Chen and Jianhui Wang
Organometallics 2013 Volume 32(Issue 6) pp:1958-1963
Publication Date(Web):March 6, 2013
DOI:10.1021/om400046r
A series of aryl-substituted pyrrole derivatives was synthesized from diallylamines through a ruthenium carbene catalyzed ring-closing metathesis reaction and in situ oxidative dehydrogenation reaction catalyzed by FeCl3·6H2O or CuCl2·2H2O in the presence of O2. The reaction was mild, simple, and convenient. An oxygen atmosphere played a critical role in obtaining high conversion of substituted pyrroles in the proposed catalytic system.
Co-reporter:Mingbo Shao;Lu Zheng;Weixia Qiao;Jingjing Wang
Advanced Synthesis & Catalysis 2012 Volume 354( Issue 14-15) pp:2743-2750
Publication Date(Web):
DOI:10.1002/adsc.201200119

Abstract

A cationic ruthenium carbyne complex was prepared and was found to initiate olefin metathesis reactions with good activities, which throws a new light on the design of a new type of ruthenium catalyst for RCM reactions. More importantly, no double bond isomerized by-product was observed even at elevated temperatures in reactions catalyzed by the new carbyne complex. A mechanism involving the in situ conversion of the ruthenium carbyne to a ruthenium carbene complex via addition of an iodide to the carbyne carbon was also proposed.

Co-reporter:Weixia Qiao, Mingbo Shao, Jianhui Wang
Journal of Organometallic Chemistry 2012 713() pp: 197-202
Publication Date(Web):
DOI:10.1016/j.jorganchem.2012.05.009
Co-reporter:Jingjing Wang;Weiqiang Chen;Sujing Zuo;Lu Liu;Xinrui Zhang ;Dr. Jianhui Wang
Angewandte Chemie 2012 Volume 124( Issue 49) pp:12500-12504
Publication Date(Web):
DOI:10.1002/ange.201206693
Co-reporter:Jingjing Wang;Weiqiang Chen;Sujing Zuo;Lu Liu;Xinrui Zhang ;Dr. Jianhui Wang
Angewandte Chemie International Edition 2012 Volume 51( Issue 49) pp:12334-12338
Publication Date(Web):
DOI:10.1002/anie.201206693
Co-reporter:Lu Zheng ;Dr. Jianhui Wang
Chemistry - A European Journal 2012 Volume 18( Issue 31) pp:9699-9704
Publication Date(Web):
DOI:10.1002/chem.201200657

Abstract

A [{RhCl(cod)}2]/CCl3COOH system was developed for the oxidative coupling of non-chelate-assisted arenes with olefins in the presence of catalytic amounts of Cu(OAc)2H2O as a co-oxidant and oxygen as the terminal oxidant. The acid was an indispensable component in this system and played a very important role in the coupling reaction. This catalytic system was applied to the direct oxidative coupling of a series of arenes and olefins and the corresponding products were afforded in high yields with special chemo- and regioselectivity. This reaction provides an atom-efficient route to vinylarenes, which are widely used in various fine chemicals.

Co-reporter:Jingjing Wang, Bowen Liu, Haitao Zhao, and Jianhui Wang
Organometallics 2012 Volume 31(Issue 24) pp:8598-8607
Publication Date(Web):December 12, 2012
DOI:10.1021/om300994j
A new rhodium-catalyzed decarbonylated coupling reaction of ethyl benzo[h]quinoline-10-carboxylate and organoboron compounds that occurs through chelation-assisted sp2 C–COOEt bond activation was described. In this system CuCl played a very important role, and a five-membered rhodacycle was also involved as a key intermediate. Various functionalities were compatible in the reaction, and the desired products were obtained in good to excellent yields. DFT calculations on the mechanisms of this reaction using a Rh(I) model catalyst have also been carried out.
Co-reporter:Guiyan Liu
Angewandte Chemie International Edition 2010 Volume 49( Issue 26) pp:4425-4429
Publication Date(Web):
DOI:10.1002/anie.200906034
Co-reporter:Guiyan Liu
Angewandte Chemie 2010 Volume 122( Issue 26) pp:4527-4531
Publication Date(Web):
DOI:10.1002/ange.200906034
Co-reporter:Guiyan Liu;Haiyan He
Advanced Synthesis & Catalysis 2009 Volume 351( Issue 10) pp:1610-1620
Publication Date(Web):
DOI:10.1002/adsc.200800713

Abstract

A ferrocene-tagged ruthenium carbene 15 that can be reversibly immobilized in an ionic liquid (IL) via the controlled oxidation and reduction of a ferrocene tag was prepared. This offers a new strategy which uses redox chemistry to control immobilization and to recycle both the catalyst and the IL. In this experiment, 11 recycles were performed for the ring-closing metathesis (RCM) of a substrate using 16 as the catalyst in an ionic liquid (IL). More importantly, after the reaction was completed, the ruthenium catalyst was easily separated from the supporting IL by just adding decamethylferrocene (DMFc) to reduce the cationic ferrocene and then extracting it with benzene. Thus, this recycle system offers an easy way to recycle both the ruthenium catalyst and the IL.

Co-reporter:Guiyan Liu, Bin Wu, Jianzheng Zhang, Xiaoli Wang, Mingbo Shao and Jianhui Wang
Inorganic Chemistry 2009 Volume 48(Issue 6) pp:2383-2390
Publication Date(Web):February 13, 2009
DOI:10.1021/ic801111h
A pyrene-tagged ruthenium carbene 8 was synthesized and immobilized on single-walled carbon nanotubes (SWNTs) via π−π stacking. These π−π interactions were greatly affected by the reaction temperature and the solvent polarity, thus, offering a new reversible immobilization model that can be controlled by reaction temperature in polar solvents, such as acetone. SWNTs-supported ruthenium carbene 8 is a robust and recyclable catalyst system. Six to seven cycles were achieved for ring-closing metathesis of selected substrates. Importantly, after the complete loss of activity, the SWNTs can be easily recycled by washing with tetrahydrofuran. The recycled SWNTs can then be reloaded with 8. The reusability of the catalyst supported on recycled SWNTs is comparable with that supported on fresh SWNTs.
Co-reporter:Guiyan Liu, Maocong Yi, Lu Liu, Jingjing Wang and Jianhui Wang
Chemical Communications 2015 - vol. 51(Issue 14) pp:NaN2914-2914
Publication Date(Web):2014/12/17
DOI:10.1039/C4CC09358E
A highly efficient one-pot procedure for the preparation of substituted quinolines from substituted o-nitrotoluenes with electron-withdrawing groups and olefins (acrylic esters and acrylonitriles) using a cesium catalyst has been developed. A plausible [2+4] cycloaddition mechanism is proposed. This method uses nitroaromatic compounds as the starting materials to give quinoline derivatives in good to high yields under mild conditions with no transition metal catalysis. It provides an atom economical pathway for the synthesis of quinoline derivatives which could be used in industrial processes.
Co-reporter:Yulian Duan, Tao Wang, Qingxiao Xie, Xiaobo Yu, Weijie Guo, Jianhui Wang and Guiyan Liu
Dalton Transactions 2016 - vol. 45(Issue 48) pp:NaN19448-19448
Publication Date(Web):2016/11/14
DOI:10.1039/C6DT03899A
A series of nitrogen chelated ruthenium carbene metathesis catalysts containing an N-heterocyclic carbene (NHC) and a carbonyl group have been developed and their catalytic activities for olefin metathesis reactions were investigated. The X-ray structure of the [(H2IMes)(Cl)2Ru]C(H)CH2[p-F(C6H3)NC(CF3)(C(O)OCH2CH3)] complex shows that the carbonyl oxygen of the ester and the imine nitrogen are both coordinated to the Ru metal to give an octahedral structure. The catalytic activity of these ruthenium carbene complexes for olefin metathesis reactions was tested. Some of the complexes bearing electron withdrawing groups had high initiation rates. These complexes exhibited excellent performance for both ring-closing metathesis and cross metathesis.
Co-reporter:Mengwei Li, Yi-Xuan Wang, Jianhui Wang and Yulan Chen
Journal of Materials Chemistry A 2017 - vol. 5(Issue 13) pp:NaN3414-3414
Publication Date(Web):2017/03/07
DOI:10.1039/C7TC00173H
A facile approach to synthesize stereospecific (Z)-aryl-functionalized 1,4-enediones has been presented. The resulting molecules (TPBD-1 and TPBD-2) were demonstrated as a new type of heteroatom-containing AIE-active luminogens with multiple sites for structural modifications. Knoevenagel reaction of TPBD-1 led to a high electron affinity cyano derivative (TPBD-CN), which showed enhanced AIE performance and pronounced red-emission. More interestingly, TPBD-1 exhibited acid-induced red emission both in dilute solution and in the solid state, which is attractive due to its great potential for turn-on optical sensing. The reversible fluorescence acid sensing can be attributed to the stepwise binding effect of carbonyl groups on the 1,4-enedione core to rigidify the molecular conformation and strengthen the D–A interaction, which was systematically investigated by UV-vis, FL, FT-IR, and NMR spectroscopy and was further corroborated by DFT calculations.
Co-reporter:Yulian Duan, Tao Wang, Qingxiao Xie, Xiaobo Yu, Weijie Guo, Shutao Wu, Danfeng Li, Jianhui Wang and Guiyan Liu
Dalton Transactions 2017 - vol. 46(Issue 18) pp:NaN5993-5993
Publication Date(Web):2017/04/04
DOI:10.1039/C7DT00853H
An indolinooxazolidine tagged N-heterocyclic carbene Ru olefin metathesis catalyst was synthesized and the molecular structure of this new Ru complex was determined by single crystal X-ray diffraction. This complex is a homogeneous catalyst and can be recovered by controlling the polarity of the indolinooxazolidine tag. Under acidic conditions the indolinooxazolidine tag exists as an open protonated form and under basic conditions the tag is in a closed form. The distribution of this catalyst in a two-phase system can be controlled by simply changing the pH, making the recovery of this catalyst easily obtainable.
6-Fluoroquinoline-8-carboxylic acid
Ethyl 2-methyl-3,5-dinitrobenzoate
2-PROPENOIC ACID, 3-(3,5-DIBROMOPHENYL)-, BUTYL ESTER, (2E)-
Benzene, [3-methyl-1-(2-propenyloxy)-3-butenyl]-
Benzenamine, 2-methyl-N,N-di-2-propenyl-