Gong-Hua Song

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Name: 宋恭华; Song, GongHua

Organization: East China University of Science and Technology , China

Department: Institute of Pesticides & Pharmaceuticals

Title: Professor(PhD)

Chemicals
References

Ligand-Free Nickel-Catalysed 1,4-Addition of Arylboronic Acids to ,-Unsaturated Carbonyl Compounds

Co-reporter:Wen Chen;Lu Sun;Xi Huang;Jiayi Wang;Yanqing Peng ;Gonghua Song

Advanced Synthesis & Catalysis 2015 Volume 357( Issue 7) pp:1474-1482

Publication Date(Web):

DOI:10.1002/adsc.201400761

Metal-free multicomponent coupling reaction of aliphatic amines, formaldehyde, organoboronic acids, and propiolic acids for the synthesis of diverse propargylamines

Co-reporter:Jiayi Wang, Qiaoying Shen, Jiayu Zhang, Gonghua Song

Tetrahedron Letters 2015 Volume 56(Issue 7) pp:903-906

Publication Date(Web):11 February 2015

DOI:10.1016/j.tetlet.2014.12.142

A metal-free multicomponent coupling reaction of aliphatic amines, formaldehyde, organoboronic acids, and propiolic acids has been reported for the synthesis of diverse propargylamines. This transformation involves a MCR2 of PBM and decarboxylative three-component coupling reactions.

Catalyst-free synthesis of N-β-hydroxyethyl pyrroles and indoles via a domino [3+2] cycloaddition and ring-opening aromatization process

Co-reporter:Jiayi Wang, Qiaoying Shen, Jiayu Zhang, Gonghua Song

Tetrahedron Letters 2015 Volume 56(Issue 22) pp:2913-2916

Publication Date(Web):27 May 2015

DOI:10.1016/j.tetlet.2015.04.074

N-β-Hydroxyethyl pyrroles and indoles were constructed from the reaction of trans-4-hydoxyproline or indoline-2-carboxylic acid with electron deficient aldehydes via a domino [3+2] cycloaddition and ring-opening aromatization process under catalyst-free conditions.

Desulfurization using the 1,2-dimethylimidazolium ionic liquid as an adsorbent

Co-reporter:Yue-Qin Cai, Gong-Hua Song, Dian-Ni Liang

Chinese Chemical Letters 2015 Volume 26(Issue 3) pp:317-319

Publication Date(Web):March 2015

DOI:10.1016/j.cclet.2014.11.027

The aim of this study is to investigate the possible use of a 1,2-dimethylimidazolium ionic liquid, 2,2-bis((1,2-dimethylimidazolium)methyl)propane-1,3-diol hexafluorophosphate (1), as an adsorbent to selectively remove aromatic heterocyclic sulfur compounds from model fuels. The result indicates that adsorbent 1 is insoluble in model fuels. The spent IL saturated sulfur compounds could be regenerated by a water dilution process. The influence of extraction time or temperature as well as the molar ratio of 1 to aromatic heterocyclic sulfur compound was also studied.2,2-Bis((1,2-dimethylimidazolium)methyl)propane-1,3-diol hexafluorophosphate (1) was synthesized and used as an adsorbent to selectively remove aromatic heterocyclic sulfur compounds from model fuels.

Direct olefination of benzaldehydes into 1,3-diarylpropenes via a copper-catalyzed heterodomino Knoevenagel-decarboxylation-Csp3-H activation sequence

Co-reporter:Yaping Zhao, Lu Sun, Tieqiang Zeng, Jiayi Wang, Yanqing Peng and Gonghua Song

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 21) pp:3493-3498

Publication Date(Web):26 Mar 2014

DOI:10.1039/C4OB00155A

Copper-catalyzed direct olefination of benzaldehydes into 1,3-diarylpropenes by a novel domino Knoevenagel-decarboxylation-Csp3-H activation sequence is reported. This method provides a concise and effective route toward the synthesis of unsymmetrical 1,3-diarylpropene derivatives.

Synthesis of tertiary propargylamines via a rationally designed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes

Co-reporter:Jiayi Wang, Qiaoying Shen, Pinzhen Li, Yanqing Peng and Gonghua Song

Organic & Biomolecular Chemistry 2014 vol. 12(Issue 30) pp:5597-5600

Publication Date(Web):17 Jun 2014

DOI:10.1039/C4OB01055H

A novel approach for the synthesis of tertiary propargylamines is achieved through a Cu(OAc)2-catalyzed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes, where a combination of PBM and A3-coupling reactions is involved in this new multicomponent reaction.

Concise synthesis of aromatic tertiary amines via a double Petasis–borono Mannich reaction of aromatic amines, formaldehyde, and organoboronic acids

Co-reporter:Jiayi Wang, Pinzhen Li, Qiaoying Shen, Gonghua Song

Tetrahedron Letters 2014 Volume 55(Issue 29) pp:3888-3891

Publication Date(Web):16 July 2014

DOI:10.1016/j.tetlet.2014.03.131

A simple and efficient strategy to construct aromatic tertiary amines via a double Petasis–borono Mannich reaction of aromatic amines, formaldehyde, and organoboronic acids has been developed. The transformation provides a useful method for the synthesis of amine derivatives.A simple and efficient strategy to construct aromatic tertiary amines via a double Petasis–borono Mannich reaction of aromatic amines, formaldehyde and organoboronic acids has been developed. The transformation provides a useful method for the synthesis of amine derivatives.

Ionic liquid-supported synthesis of piperazine derivatives as potential insecticides

Co-reporter:Yan Shen;Jia-Yi Wang

Molecular Diversity 2014 Volume 18( Issue 1) pp:195-202

Publication Date(Web):2014 February

DOI:10.1007/s11030-013-9492-4

With the purpose of extending our efforts on the search and synthesis of new insecticides with novel acting modes, a series of novel 4-(2-(4-(pyridin-2-yl)piperazin-1-yl)ethoxy)aniline derivatives were designed based on classical serotonin receptor ligands and synthesized through the rapid ionic liquid-supported parallel synthesis with yields up to 88 %. These products were purified through the convenient washing with appropriate solvents and isolated in good yield. In addition, 27 amide or urea derivatives of anilines were also prepared. Bioassay data showed that some of the synthesized compounds displayed selective insecticidal bioactivities against tested pests.

A simple and efficient synthesis of fused morpholine pyrrolidines/piperdines with potential insecticidal activities

Co-reporter:Jiayi Wang;Beiling Xu;Shanyu Si;Hui Li;Gonghua Song

Molecular Diversity 2014 Volume 18( Issue 4) pp:887-893

Publication Date(Web):2014 November

DOI:10.1007/s11030-014-9531-9

A simple and efficient synthesis of fused morpholine pyrrolidine/piperdine core structures was accomplished via a Petasis-borono Mannich reaction of cyclic amino alcohols, glyoxal and arylboronic acids with moderate to good yields. The bioassay data showed that the synthesized compounds displayed selective insecticidal activities against armyworm and root-knot nematode.

Investigation on the Coordination Mode of IL-Supported Diols Used as Phosphine-Free Ligands for Palladium Catalyzed Heck Reaction

Co-reporter:Yueqin Cai;Gonghua Song;Xiao Chen

Chinese Journal of Chemistry 2013 Volume 31( Issue 10) pp:1250-1256

Publication Date(Web):

DOI:10.1002/cjoc.201300461

Abstract

The coordination mode of IL-supported diols used as phosphine-free ligands for palladium catalyzed Heck reaction has been investigated by tuning their compositions. The difference in coordination of these IL-supported diols with metal Pd in Heck reaction was related to the changes of the cation rings, leading to the different activities of Pd catalyst in the reaction. The experimental results indicated that the activities of Pd catalyst were affected mainly by π-electron density of the cation rings. Compared to pyridinium and piperidinium cations, imidazolium cations showed the best coordination to metal Pd. In the meantime, C-2 hydrogen and the length of alkyl side chains had impacts on the coordination as well.

Palladium nanoparticles supported on functional ionic liquid modified magnetic nanoparticles as recyclable catalyst for room temperature Suzuki reaction

Co-reporter:Jiayi Wang, Beiling Xu, Haiyang Sun, Gonghua Song

Tetrahedron Letters 2013 Volume 54(Issue 3) pp:238-241

Publication Date(Web):16 January 2013

DOI:10.1016/j.tetlet.2012.11.009

Palladium nanoparticles were successfully immobilized on amine functionalized ionic liquid modified magnetic nanoparticles leading to a magnetically recoverable Pd catalyst, which exhibits high catalytic activity in the Suzuki coupling reaction at room temperature. The catalyst can be separated from the reaction mixture by applying a permanent magnet externally and can be reused for several times without significant loss of activity.Figure optionsDownload full-size imageDownload as PowerPoint slide

Polymerized functional ionic liquid supported Pd nanoparticle catalyst for reductive homocoupling of aryl halides

Co-reporter:Jiayi Wang;Yuan Li;Pinzhen Li;Gonghua Song

Monatshefte für Chemie - Chemical Monthly 2013 Volume 144( Issue 8) pp:1159-1163

Publication Date(Web):2013 August

DOI:10.1007/s00706-013-0925-7

Homopolymer of 3-(cyanomethyl)-1-vinylimidazolium hexafluorophosphate was synthesized and used as a support for Pd nanoparticles. The Pd@poly-CN-PF6 catalyst (2 mol % Pd) selectively catalyzes the reductive homocoupling reaction of aryl iodides and bromides at 100 °C in water, and the catalyst can be recycled and reused several times with slight loss of activity.

FeCl3-promoted synthesis of 1,3,4-thiadiazoles under combined microwave and ultrasound irradiation in water

Co-reporter:Huangdi Feng;Xili Ying;Yanqing Peng

Monatshefte für Chemie - Chemical Monthly 2013 Volume 144( Issue 5) pp:681-686

Publication Date(Web):2013 May

DOI:10.1007/s00706-012-0846-x

An eco-friendly and efficient synthesis of substituted 1,3,4-thiadiazole derivatives has been developed. This aqueous heterogeneous approach proceeds smoothly and quickly under combined microwave and ultrasound irradiation in the presence of FeCl3.

Aqueous-Phase, Palladium-Catalyzed Heck Reaction: The Significant Role of CN-containing Counter Anion

Co-reporter:Yueqin Cai;Gonghua Song;Xiaoying Zhou

Chinese Journal of Chemistry 2012 Volume 30( Issue 12) pp:2819-2822

Publication Date(Web):

DOI:10.1002/cjoc.201200675

Abstract

Water-soluble diol-functionalized imidazolium ionic liquid 1, prepared from 2,2-bis(1-methyl-methyl-imidazolium)propane-1,3-diol bromide, potassium hydroxide, and malononitrile, was used as an efficient phosphine-free ligand for palladium-catalyzed arylation of aryl halides with acrylates in aqueous phase under mild conditions. It was found that the synergistic coordinating action of diol-functionalized imidazolium cation with CN-containing anion played the key role in improving the activity and stability of the catalyst.

Synthesis of polysubstituted pyridines under combined microwave and ultrasound irradiation: K2CO3-promoted tandem addition/cyclization/hydrogen shift process

Co-reporter:Huangdi Feng, Yuan Li, Erik V. Van der Eycken, Yanqing Peng, Gonghua Song

Tetrahedron Letters 2012 Volume 53(Issue 9) pp:1160-1162

Publication Date(Web):29 February 2012

DOI:10.1016/j.tetlet.2011.12.103

A convenient and efficient K2CO3-promoted tandem reaction of chalcone, malononitrile, and methanol for the synthesis of highly functionalized pyridines has been developed. This multi-component reaction employing the weak nucleophilic agent methanol proceeded smoothly under combined microwave and ultrasound irradiation (CMUI). The reaction mechanism was proposed to consist of a Michael addition, a methoxylation of CN bond, a cyclization to a 1,4-dihydropyridine and an intermolecular hydrogen shift between 1,4-dihydropyridine and initial chalcone.

Synthesis and Insecticidal Activities of Chlorothiazolyl Analogs of Nitromethylene Neonicotinoids with Tetrahydropyridine Fixed cis-Configuration

Co-reporter:Xusheng Shao;Xinglong Huang;Qian Shi;Zhong Li;Liming Tao ;Gonghua Song

Journal of Heterocyclic Chemistry 2012 Volume 49( Issue 5) pp:1136-1142

Publication Date(Web):

DOI:10.1002/jhet.969

The chlorothiazolyl moiety was an effective bioisoster of chloropyridyl in pesticide molecular design. Replacement of chloropyridyl in cis-nitromethylene neonicotinoids with chlorothiazolyl generated the chlorothiazolyl counterpart of nitromethylene neonicotinoids with tetrahydropyridine fixed cis-configuration. Bioassay against cowpea aphis (Aphis craccivora) indicated that the chlorothiazolyl analogs could maintain the high insecticidal activity.

Fe3O4 Nanoparticle-Supported Copper(I) Pybox Catalyst: Magnetically Recoverable Catalyst for Enantioselective Direct-Addition of Terminal Alkynes to Imines

Co-reporter:Tieqiang Zeng, Luo Yang, Reuben Hudson, Gonghua Song, Audrey R. Moores, and Chao-Jun Li

Organic Letters 2011 Volume 13(Issue 3) pp:442-445

Publication Date(Web):December 28, 2010

DOI:10.1021/ol102759w

An Fe3O4 nanoparticle-supported copper(I) pybox catalyst, which exhibits excellent reactivity and yields products with good enantioselectivity, was developed. As a proof of concept, six optically active propargyl amines were obtained in excellent yields. The catalyst can be magnetically removed and recycled easily six times without a decrease in activity or enantioselectivity.

Reusable Pd nanoparticles immobilized on functional ionic liquid co-polymerized with styrene for Suzuki reactions in water–ethanol solution

Co-reporter:Jiayi Wang, Gonghua Song, Yanqing Peng

Tetrahedron Letters 2011 Volume 52(Issue 13) pp:1477-1480

Publication Date(Web):30 March 2011

DOI:10.1016/j.tetlet.2011.01.092

Co-polymer of 3-(2,3-dihydroxypropyl)-1-vinylimidazolium chloride and styrene was synthesized and used as a support of Pd nanoparticles. The Pd@poly-Sty-co-diOH-Cl catalyst can efficiently catalyze Suzuki reactions for a wide range of aryl iodides and bromides with 0.05 mol % Pd at 70 °C in water–ethanol solution under air, and the catalyst can be recycled and reused for several times without significant loss of activity.

Silica-supported sulfonic acid-functionalized ionic liquid coated with [bmim][PF6] as a scavenger for the synthesis of amides

Co-reporter:Li-Qin Kang;Yue-Qin Cai;Yan-Qing Peng;Xi-Li Ying

Molecular Diversity 2011 Volume 15( Issue 1) pp:109-113

Publication Date(Web):2011 February

DOI:10.1007/s11030-010-9261-6

The methodology of using a silica gel-supported functionalized ionic liquid as a scavenger in the purification of parallel synthesis products was demonstrated. Silica-supported sulfonic acid-functional ionic liquid was synthesized by etherification, aminate, and quaternary aminate from activated silica gel and 3-chloropropyl trimethoxysilane, imidazole, and 1,4-butanesultone, which was followed by acidification using trifluoromethanesulfonic acid and anion exchange with potassium hexafluorophosphate. A conventional ionic liquid, 1-butyl-3-methylimidazolium hexafluorophosphate was then used to coat the surface of the silica gel. The silica-supported functionalized ionic liquid was used as a scavenger in the removal of excess amine in the parallel synthesis of amides. Desired products were obtained in excellent yields and purity with a sequestration time of less than 100 min at room temperature. After scavenging, the scavenger was easily filtered out and regenerated.

Synthesis, biological assay in vitro and molecular docking studies of new imidazopyrazinone derivatives as potential dipeptidyl peptidase IV inhibitors

Co-reporter:Yanyun Zhu, Shuang Xia, Mingjie Zhu, Weiyin Yi, Jiagao Cheng, Gonghua Song, Zhong Li, Peng Lu

European Journal of Medicinal Chemistry 2010 Volume 45(Issue 11) pp:4953-4962

Publication Date(Web):November 2010

DOI:10.1016/j.ejmech.2010.08.002

A series of novel imidazopyrazinone derivatives were synthesized and evaluated with regard to their ability to inhibit dipeptidyl peptidase IV (DPP-IV) in vitro. Of these compounds (2R)-4-oxo-4-[2-(3-carbamoylbenzyl)-hexahydro-3-oxoimidazo [1,5-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine fumaric acid (17h, IC50 = 78 nM) was shown to effectively inhibit the activity of the dipeptidyl peptidase IV enzyme. Molecular docking studies were also performed to illustrate the binding mode of compounds 15c and 17h. Favorable interactions were identified from the binding of inhibitor 15c with DPP-IV. By analogy to the binding mode of compound 15c, it seems that the introduction of a substituted benzyl moiety onto the imidazopyrazinone could remarkably improve the inhibitory activity of compound 17h.A series of novel imidazopyrazinone analogues were synthesised and evaluated for their in vitro ability to DPP-IV. Molecular docking studies were also performed.

Design and Synthesis of Novel Insecticides Based on the Serotonergic Ligand 1-[(4-Aminophenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]piperazine (PAPP)†

Co-reporter:Mingyi Cai, Zhong Li, Feng Fan, Qingchun Huang, Xusheng Shao and Gonghua Song

Journal of Agricultural and Food Chemistry 2010 Volume 58(Issue 5) pp:2624-2629

Publication Date(Web):December 10, 2009

DOI:10.1021/jf902640u

1-[(4-Aminophenyl)ethyl]-4-[3-(trifluoromethyl)phenyl]piperazine (PAPP) is a 5-HT1A agonist and was reported to display high affinity for serotonin (5-HT) receptor from the parasitic nematode Haemonchus contortus. The present investigation explored the possibility of using PAPP as a lead compound of new insecticides with novel mode of action. On the basis of the PAPP scaffold, a series of 1-arylmethyl-4-[(trifluoromethyl)pyridin-2-yl]piperazine derivatives were designed, synthesized, and evaluated for biological activities against the armyworm Pseudaletia separata (Walker). Bioassays showed that most of the target compounds displayed certain growth-inhibiting activities or larvicidal activities against armyworm. The quantitative structure−activity relationship (QSAR) for growth-inhibiting activities was also analyzed and established.

Separation, recovery and reuse of N-heterocyclic carbene catalysts in transesterification reactions

Co-reporter:Tieqiang Zeng, Gonghua Song and Chao-Jun Li

Chemical Communications 2009 (Issue 41) pp:6249-6251

Publication Date(Web):03 Sep 2009

DOI:10.1039/B910162D

A novel and convenient strategy to separate, recover and reuse N-heterocyclic carbene catalysts in transesterification reactions has been developed.

Surface cleaning under combined microwave and ultrasound irradiation: flash synthesis of 4H-pyrano[2,3-c]pyrazoles in aqueous media

Co-reporter:Yanqing Peng, Gonghua Song and Ruiling Dou

Green Chemistry 2006 vol. 8(Issue 6) pp:573-575

Publication Date(Web):18 May 2006

DOI:10.1039/B601209D

A clean, rapid and energy-efficient approach to solid–aqueous heterogeneous reactions was developed utilizing the synergistic effect of microwave and ultrasound irradiation. The dramatic acceleration in reaction rates might be explained by the removal of a passivation coating on the substrate particles and the resultant enhancement in mass and heat transfer.

Efficient and mild room temperature reduction of benzophenones under ultrasound irradiation

Co-reporter:Yanqing Peng, Wujun Zhong, Gonghua Song

Ultrasonics Sonochemistry 2005 Volume 12(Issue 3) pp:169-172

Publication Date(Web):February 2005

DOI:10.1016/j.ultsonch.2003.12.002

Benzophenones without strong electron-releasing substituents were reduced into the corresponding benzhydrols at room temperature in moderate to good yields with Zn–NaOH-95% ethanol under ultrasound irradiation. This method is also propitious to the synthesis of 3-phenylphthalide and its derivates.

Combined microwave and ultrasound accelerated Knoevenagel–Doebner reaction in aqueous media: a green route to 3-aryl acrylic acids

Co-reporter:Yanqing Peng and Gonghua Song

Green Chemistry 2003 vol. 5(Issue 6) pp:704-706

Publication Date(Web):22 Oct 2003

DOI:10.1039/B310388A

The microwave and ultrasound combined aqueous Knoevenagel–Doebner reaction proves an efficient and eco-friendly route for preparing 3-aryl acrylic acids in good yields. This organic solvent-free protocol is valuable since rapid reaction rate, low energy consumption, waste minimization, simple operation and easier product work-up can be achieved.

Combined microwave and ultrasound assisted Williamson ether synthesis in the absence of phase-transfer catalysts

Co-reporter:Yanqing Peng and Gonghua Song

Green Chemistry 2002 vol. 4(Issue 4) pp:349-351

Publication Date(Web):04 Jul 2002

DOI:10.1039/B201543A

The combined microwave and ultrasound assisted Williamson reaction proves an efficient and ecologically valuable route for preparing ethers in the absence of organic auxiliary substances such as phase-transfer catalysts.

Simultaneous microwave and ultrasound irradiation: a rapid synthesis of hydrazides

Co-reporter:Yanqing Peng and Gonghua Song

Green Chemistry 2001 vol. 3(Issue 6) pp:302-304

Publication Date(Web):06 Nov 2001

DOI:10.1039/B108878P

Hydrazinolysis of esters is dramatically promoted by simultaneous microwave and ultrasound irradiation using an innovative and efficient reaction apparatus.

Synthesis of tertiary propargylamines via a rationally designed multicomponent reaction of primary amines, formaldehyde, arylboronic acids and alkynes

Co-reporter:Jiayi Wang, Qiaoying Shen, Pinzhen Li, Yanqing Peng and Gonghua Song

Organic & Biomolecular Chemistry 2014 - vol. 12(Issue 30) pp:NaN5600-5600

Publication Date(Web):2014/06/17

DOI:10.1039/C4OB01055H

Separation, recovery and reuse of N-heterocyclic carbene catalysts in transesterification reactions

Co-reporter:Tieqiang Zeng, Gonghua Song and Chao-Jun Li

Chemical Communications 2009(Issue 41) pp:NaN6251-6251

Publication Date(Web):2009/09/03

DOI:10.1039/B910162D

A novel and convenient strategy to separate, recover and reuse N-heterocyclic carbene catalysts in transesterification reactions has been developed.

Direct olefination of benzaldehydes into 1,3-diarylpropenes via a copper-catalyzed heterodomino Knoevenagel-decarboxylation-Csp3-H activation sequence