Co-reporter:Xuan Zhou;Wanyong Fu;Hongshuo Jiang;Chenglong Wang;Chao Ju;Wenyi Chu
Organic & Biomolecular Chemistry 2017 vol. 15(Issue 9) pp:1956-1960
Publication Date(Web):2017/03/01
DOI:10.1039/C6OB02707E
A novel synthetic protocol for the construction of eight-membered heterocycles by intramolecular palladium-catalyzed ortho C–H activation/C–C cyclization was proposed. With protosappanin A as the lead compound, 25 derivatives of 8-azaprotosappanin A were prepared in good yields by this protocol. Besides, a plausible reaction mechanism of the intramolecular cyclization was proposed. This strategy could be widely used in the synthesis of some natural products and drugs with large heterocycles due to the fast reaction rate and the mild conditions. In vitro antimicrobial activities of the synthesized compounds were assessed against the strains of Gram-positive bacteria and linezolid and ciprofloxacin were selected as the standard drugs. Some of the synthesized compounds were found to have excellent antibacterial activities.
Co-reporter:Huatao Han;Hongyan Zhao;Yang Liu;Zhuofei Li;Jinyi Song;Wenyi Chu
RSC Advances (2011-Present) 2017 vol. 7(Issue 7) pp:3790-3795
Publication Date(Web):2017/01/09
DOI:10.1039/C6RA26309G
A sustainable and efficient catalyst for converting carbohydrates to a renewable platform chemical 5-hydroxymethylfurfural (HMF) is the goal in the study of biomass recycling. Reduced graphene oxide-supported tungsten trioxide (WO3/RGO) as an acidic catalyst was synthesized through a one-step hydrothermal method, characterized via TEM, XPS, XRD and Raman spectroscopy and applied to the conversion of fructose to HMF. The WO3/RGO catalyst showed a highly efficient catalytic activity, and the yield of HMF could reach up to 84.2% with complete conversion of fructose. The catalyst could be reused five times with a slight decrease in activity. Further study indicated that WO3/RGO could also catalyze the conversion of cellulose, glucose and sucrose to HMF.
Co-reporter:Zhuofei Li, Hongyan Zhao, Huatao Han, Yang Liu, Jinyi Song, Weihao Guo, Wenyi Chu, Zhizhong Sun
Tetrahedron Letters 2017 Volume 58, Issue 42(Issue 42) pp:
Publication Date(Web):18 October 2017
DOI:10.1016/j.tetlet.2017.09.011
•ZnO nanoparticles supported on reduced graphene oxide were prepared.•ZnO/RGO as catalyst was applied to the Claisen-Schmidt condensation.•A new catalytic system was developed under microwave conditions.•ZnO/RGO could be recycled without obvious losses of catalytic activity.ZnO nanoparticles supported on reduced graphene oxide (ZnO/RGO) were prepared by the hydrothermal method and characterized by TEM, XPS, XRD, and Raman spectroscopy. As a green catalyst, ZnO/RGO was applied to the Claisen-Schmidt condensation reaction of aryl aldehydes and aryl ketones under microwave irradiation. Therein, chalcone products could be efficiently synthesized and easily separated from the heterogeneous catalysis system. The catalyst could be recycled four times without significant loss of catalytic activity.Download high-res image (169KB)Download full-size image
Co-reporter:He Song;Xiaochong Liu;Chenglong Wang;Jingyi Qiao; Wenyi Chu; Zhizhong Sun
Asian Journal of Organic Chemistry 2017 Volume 6(Issue 11) pp:1693-1698
Publication Date(Web):2017/11/01
DOI:10.1002/ajoc.201700418
AbstractA protocol for the Cu(TFA)2-catalyzed (TFA=trifluoroacetic acid) picolinamido-directed C8−H cyanation of naphthalene derivatives with benzoyl cyanide as the cyano source has been developed. A series of 8-cyano-1-(picolinamido)naphthalene derivatives were efficiently obtained in moderate to good yields by using this method. We prepared a total of 22 products, 10 of which have not previously been reported. Benzoyl cyanide was originally employed for the C(sp2)−H cyanation of arenes. The picolinamide moiety served a critical role as the directing group in this cyanation reaction of naphthalenes.
Co-reporter:Jiaqi Liu, Xuan Zhou, Chenglong Wang, Wanyong Fu, Wenyi Chu and Zhizhong Sun
Chemical Communications 2016 vol. 52(Issue 29) pp:5152-5155
Publication Date(Web):09 Mar 2016
DOI:10.1039/C6CC01149G
A total synthesis method for protosappanin A, which is a complex natural product with many biological activities, was developed with 6 linear steps. Dibenzo[b,d]oxepinones as the key intermediates of the synthetic route were prepared by a palladium-catalyzed ortho C–H activation/C–C cyclization under microwave irradiation. 25 derivatives of protosappanin A were obtained.
Co-reporter:Hongyan Zhao, Guijie Mao, Huatao Han, Jinyi Song, Yang Liu, Wenyi Chu and Zhizhong Sun
RSC Advances 2016 vol. 6(Issue 47) pp:41108-41113
Publication Date(Web):21 Apr 2016
DOI:10.1039/C6RA04683E
As an outstanding mesh catalyst support, reduced graphene oxide (RGO) has attracted enormous attention in recent years. Cu nanoparticles-RGO (Cu NPs@RGO) as a green catalyst was prepared through a green reduction method by ascorbic acid in N-methyl-2-pyrrolidone. The structure of prepared Cu NPs@RGO was characterized. The catalytic activity of Cu NPs@RGO was estimated. A green and efficient method for synthesizing symmetrical biaryl compounds was developed by Cu NPs@RGO-catalyzed Ullmann homocoupling of aryl halides or arylboronic acids in ionic liquids under microwave (MW) irradiation. The catalytic system could be recycled five times with slight loss of activity. Through this method, nine kinds of biaryls were prepared by homocoupling reaction of the corresponding aryl iodides, aryl bromides, aryl chlorides and aryl boronic acids in moderate to good yields.
Co-reporter:Lu Han, Yahui Wang, He Song, Huatao Han, Lulu Wang, Wenyi Chu and Zhizhong Sun
RSC Advances 2016 vol. 6(Issue 25) pp:20637-20643
Publication Date(Web):08 Feb 2016
DOI:10.1039/C6RA00163G
A mild, practical and efficient palladium-catalyzed decarboxylative ortho-aroylation of N-acetyl-1,2,3,4-tetrahydroquinolines with α-oxoarylacetic acids via C–H bond activation is described. This protocol provides efficient access to a series of C8-aroyl terahydroquinolines.
Co-reporter:Limin Ren;Wenyi Chu;Dinghui Guan;Yanjun Hou;Man Wang;Xiaobin Yuan
Applied Organometallic Chemistry 2014 Volume 28( Issue 9) pp:673-677
Publication Date(Web):
DOI:10.1002/aoc.3180
A simple and efficient route for the preparation of terphenyl derivatives via palladium-catalyzed sequential directed C―H arylation/Suzuki–Miyaura cross-coupling in ‘one-pot’ has been developed. 4,4′-(Cyclohexane-1,1-diyl)diphenol is an essential ligand. This reaction can tolerate a series of functional groups and provides the terphenyl derivatives in moderate to good yield. Copyright © 2014 John Wiley & Sons, Ltd.
Co-reporter:Jing Shi, Yanjun Hou, Wenyi Chu, Xiaohong Shi, Huiquan Gu, Bilin Wang, and Zhizhong Sun
Inorganic Chemistry 2013 Volume 52(Issue 9) pp:5013-5022
Publication Date(Web):April 19, 2013
DOI:10.1021/ic302726z
A new bis(β-diketonate), 1,3-bis(4,4,4-trifluoro-1,3-dioxobutyl)phenyl (BTP), which contains a trifluorinated alkyl group, has been prepared for the synthesis of two series of dinuclear lanthanide complexes with the general formula Ln2(BTP)3L2 [Ln3+ = Eu3+, L = DME(1), bpy(2), and phen(3); Ln3+ = Sm3+, L = DME(4), bpy(5), and phen(6); DME = ethylene glycol dimethyl ether, bpy = 2,2′-bipyridine, phen = 1,10-phenanthroline]. The crystal structure of the free ligand has been determined and shows a twisted arrangement of the two binding sites around the 1,3-phenylene spacer. X-ray crystallographic analysis reveals that complexes 1, 2, 4, and 5 are triple-stranded dinuclear structures formed by three bis-bidentate ligands with two lanthanide ions. The room-temperature photoluminescence (PL) spectra of complexes 1–6 show that this bis-β-diketonate can effectively sensitize rare earths (Sm3+ and Eu3+) and produce characteristic emissions of the corresponding Eu3+ and Sm3+ ions. In addition, two bidentate nitrogen ancillary ligands, 2,2′-bipyridine (bpy) and 1,10-phenanthroline (phen), have been employed to enhance the luminescence quantum yields and lifetimes of both series of Eu3+ and Sm3+ complexes.
Co-reporter:Yanjun Hou;Jing Shi;Wenyi Chu
European Journal of Inorganic Chemistry 2013 Volume 2013( Issue 17) pp:3063-3069
Publication Date(Web):
DOI:10.1002/ejic.201300013
Abstract
A bis(β-diketone), 1,3-bis(4,4,4-trifluoro-1,3-dioxobutyl)phenyl (BTP), which contains a trifluorinated alkyl group, has been exploited to obtain three series of visible-light sensitive dinuclear rare-earth complexes with the general formula [Ln2(BTP)3L2] [Ln = Nd, L = DME (1), bpy (2), and phen (3); Ln = Yb, L = DME (4), bpy (5), and phen (6); Ln = Er, L = DME (7); DME = ethylene glycol dimethyl ether, bpy = 2,2′-bipyridine, phen = 1,10-phenanthroline]. An X-ray crystallographic analysis revealed that complexes 1, 2, 4, 5, and 7 are triple-stranded helical dinuclear structures that are formed by three bis(bidentate) ligands with two lanthanide ions. The room-temperature near-IR luminescent properties of complexes 1–6 show that this bis(β-diketone) can effectively sensitize rare earths (Nd3+, Yb3+) and produce typical near-infrared luminescence upon excitation with visible light of the corresponding Nd3+ and Yb3+ ions. Additionally, two bidentate nitrogen ancillary ligands, 2,2-bipydine (bpy) and 1,10-phenanthroline (phen), have been applied to enhance the NIR luminescent properties.
Co-reporter:Wenyi Chu;Xinmin Li;Yanjun Hou;Hua Wang;Hongyu Li;Xiaobin Yuan
Applied Organometallic Chemistry 2012 Volume 26( Issue 9) pp:478-482
Publication Date(Web):
DOI:10.1002/aoc.2891
Pd/C-catalyzed Suzuki–Miyaura cross-coupling between aryl bromides and arylboronic acids in 50% methanol aqueous solution proceeded smoothly in the presence of 18-crown-6. Various aryl bromides bearing electron-withdrawing groups and electron-donating groups coupled with arylboronic acid in high yields. In addition, the catalyst could be recycled five times without loss of activity. Copyright © 2012 John Wiley & Sons, Ltd.
Co-reporter:Jiaqi Liu, Xuan Zhou, Chenglong Wang, Wanyong Fu, Wenyi Chu and Zhizhong Sun
Chemical Communications 2016 - vol. 52(Issue 29) pp:NaN5155-5155
Publication Date(Web):2016/03/09
DOI:10.1039/C6CC01149G
A total synthesis method for protosappanin A, which is a complex natural product with many biological activities, was developed with 6 linear steps. Dibenzo[b,d]oxepinones as the key intermediates of the synthetic route were prepared by a palladium-catalyzed ortho C–H activation/C–C cyclization under microwave irradiation. 25 derivatives of protosappanin A were obtained.
Co-reporter:Xuan Zhou, Wanyong Fu, Hongshuo Jiang, Chenglong Wang, Chao Ju, Wenyi Chu and Zhizhong Sun
Organic & Biomolecular Chemistry 2017 - vol. 15(Issue 9) pp:NaN1960-1960
Publication Date(Web):2017/02/01
DOI:10.1039/C6OB02707E
A novel synthetic protocol for the construction of eight-membered heterocycles by intramolecular palladium-catalyzed ortho C–H activation/C–C cyclization was proposed. With protosappanin A as the lead compound, 25 derivatives of 8-azaprotosappanin A were prepared in good yields by this protocol. Besides, a plausible reaction mechanism of the intramolecular cyclization was proposed. This strategy could be widely used in the synthesis of some natural products and drugs with large heterocycles due to the fast reaction rate and the mild conditions. In vitro antimicrobial activities of the synthesized compounds were assessed against the strains of Gram-positive bacteria and linezolid and ciprofloxacin were selected as the standard drugs. Some of the synthesized compounds were found to have excellent antibacterial activities.