Publications by authors named "Yange Huang"

9 Publications

  • Page 1 of 1

Palladium-Catalyzed Monoarylation of Arylhydrazines with Aryl Tosylates.

J Org Chem 2020 11 24;85(22):14664-14673. Epub 2020 Sep 24.

Shenzhen Municipal Key Laboratory of Chemical Synthesis of Medicinal Organic Molecules, Shenzhen Research Institute, The Chinese University of Hong Kong, No. 10, Second Yuexing Road, Shenzhen 518507, China.

A palladium-catalyzed C-N bond coupling reaction between arylhydrazines and aryl tosylates for facile synthesis of unsymmetrical ,-diarylhydrazines has been developed. Employing the catalyst system of Pd(TFA) associated with newly developed phosphine ligand , the monoarylation of arylhydrazine proceeds smoothly to afford desired products in good-to-excellent yields (up to 95%) with good functional group compatibility. This method provides an alternative synthetic pathway for accessing structurally diversified ,-diarylhydrazines from simple and easily accessible coupling components.
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http://dx.doi.org/10.1021/acs.joc.0c01599DOI Listing
November 2020

Comparison of different extraction methods for polysaccharides from Crataegus pinnatifida Bunge.

Int J Biol Macromol 2020 May 9;150:1011-1019. Epub 2019 Nov 9.

Jiangsu Key Laboratory of Regional Resource Exploitation and Medicinal Research, Huaiyin Institute of Technology, Huai'an 223003, PR China. Electronic address:

In this study, different extraction methods of polysaccharides from Crataegus pinnatifida Bunge (CPP) were compared by studying the extraction yield, structural characteristics and antioxidant activities. Firstly, polysaccharides were obtained using hot water extraction (CPPh), ultrasound assisted extraction (CPPu), enzyme assisted extraction (CPPe) and enzyme-ultrasound assisted extraction (CPPc), respectively. Meanwhile, the optimum extraction conditions of enzyme-ultrasonic assisted extraction were determined by response surface method (RSM). The extraction yields, structural characteristics and antioxidant activities were investigated and compared by visual photos, gas chromatography, ultraviolet-visible and Fourier-transform infrared spectroscopy. The results clearly showed that enzyme-ultrasonic assisted extraction possessed the highest extraction yield (10.39 ± 0.04%). The molecular weight of CPPh was the highest while the other polysaccharides had no significant difference. Besides, the monosaccharide composition of CPPc, CPPh, CPPu and CPPe were similar but the molar percentages of monosaccharide were different. Finally, the results of antioxidant activities showed that CPPc exhibited the highest scavenging effect of superoxide radical and lipids inhibiting ability. In summary, enzyme-ultrasonic assisted extraction was a high-efficient and low-energy consumption method for CPP extraction.
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http://dx.doi.org/10.1016/j.ijbiomac.2019.11.056DOI Listing
May 2020

A mild and efficient extraction method for polysaccharides from Sinonovacula constricta and study of their structural characteristic and antioxidant activities.

Int J Biol Macromol 2020 Jan 31;143:913-921. Epub 2019 Oct 31.

Jiangsu Key Laboratory of Regional Resource Exploitation and Medicinal Research, Huaiyin Institute of Technology, Huai'an 223003, PR China; Department of Resources Science of Traditional Chinese Medicines, State Key Laboratory of Modern Chinese Medicines, China Pharmaceutical University, Nanjing 210009, Jiangsu, PR China. Electronic address:

The aim of this paper is to develop a mild and efficient extraction method for polysaccharides from Sinonovacula constricta (SCP) using enzyme extraction, and analyze the structural characteristics and antioxidant activities of the two purified polysaccharide fractions (SCP-1 and SCP-2). Firstly, enzyme extraction conditions were optimized, and the conditions were found to be, as follows: enzymolysis time 173.0 min, pH 8.2, enzymolysis temperature 50.0 ℃ and enzyme content 4.0%. Comparison between enzymatic extraction and water extraction was obtained from visual, UV-visible and IR spectrum images. The results clearly indicate that there is no significant difference between them with regard to the composition of the SCP fraction, but the polysaccharide content produced by enzymatic extraction is higher. Then, the physicochemical properties and structural characteristics of SCP-1 and SCP-2 were investigated using FT-TR, UV, GC and HPGPC. The carbohydrate content, sulfuric radicals and uronic acids of the two fractions were detected. Both SCP-1 and SCP-2 were mainly consisted of glucose, but their molecular weights were different. In addition, compared the Fe chelating activity, ABTS radical and superoxide radical scavenging activity, and lipid peroxidation inhibition activity of SCP-1 and SCP-2, it turned out that SCP-2 had stronger antioxidant activity than SCP-1.
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http://dx.doi.org/10.1016/j.ijbiomac.2019.10.032DOI Listing
January 2020

Electrochemical Oxidative Aryl(alkyl)trifluoromethylation of Allyl Alcohols via 1,2-Migration.

Org Lett 2019 Jun 30;21(12):4619-4622. Epub 2019 May 30.

College of Chemistry and Molecular Sciences, the Institute for Advanced Studies (IAS) , Wuhan University , Wuhan , Hubei 430072 , People's Republic of China.

An electrochemical oxidative difunctionalization of allyl alcohols for the synthesis of β-trifluoromethyl ketones is achieved through a 1,2-migration process. A series of β-trifluoromethyl ketones can be facilely obtained utilizing CFSONa as a radical source, eliminating the use of metals and sacrificial chemical oxidants. Importantly, this protocol not only realizes aryl migration but also offers alkyl-migration products. Additionally, an electrochemically catalyzed ring expansion and gram-scale reaction demonstrated the synthetic usefulness of this protocol.
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http://dx.doi.org/10.1021/acs.orglett.9b01518DOI Listing
June 2019

Size-controllable ultrafine palladium nanoparticles immobilized on calcined chitin microspheres as efficient and recyclable catalysts for hydrogenation.

Nanoscale 2018 Aug;10(30):14719-14725

College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.

In the present work, chitin microspheres were impregnated at different concentrations of palladium salt solution to generate the precursor-Pd2+/chitin, and then a series of size-controllable palladium nanocatalysts ([email protected]) were successfully constructed by calcining the composite microspheres. Transmission electron microscopy (TEM) and X-ray absorption spectroscopy (XAS) provided reliable evidence for well-dispersed and ultrafine palladium nanoparticles (Pd NPs) with mean diameters from about 1 to 3 nm. Chitin microspheres, as the supporting framework of these catalysts, played a significant role for stabilizing the highly dispersed Pd NPs based on their abundant functional groups and large surface areas. Moreover, the chitin matrix acted as a reductant for the precursor-Pd2+ during calcination, and the calcination process made [email protected] more stable. These [email protected] catalysts were further tested for the hydrogenations of styrene and benzaldehyde, and they displayed superior catalytic activities compared to commercial Pd/C and unsupported homogeneous Pd(OAc)2 catalysts. Notably, the most active catalyst of 1.2 wt% [email protected] had a highly competitive turnover frequency (TOF) of 50 000 h-1 in the hydrogenation of styrene, and the catalyst could be repeatedly used for more than 10 cycles with no decay of the catalytic activity, suggesting potential industrial applications.
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http://dx.doi.org/10.1039/c8nr03215gDOI Listing
August 2018

Preparation of purified fractions for polysaccharides from Monetaria moneta Linnaeus and comparison their characteristics and antioxidant activities.

Int J Biol Macromol 2018 Mar 6;108:342-349. Epub 2017 Dec 6.

Jiangsu Key Laboratory of Regional Resource Exploitation and Medicinal Research, Huaiyin Institute of Technology, Huai'an, 223003, Jiangsu, PR China; Jiangsu Provincial Key Laboratory of Palygorskite Science and Applied Technology, Huaiyin Institute of Technology, Huai'an, 223003, Jiangsu, PR China. Electronic address:

The aim of this paper was to prepare purified fractions of polysaccharides from Monetaria moneta Linnaeus and further compare their characteristics and antioxidant activities. Firstly, three novel purified fractions, named MM-P1, MM-P2 and MM-P3, were successfully prepared by a DEAE-Sepharose fast-flow column. Then, their characteristics were compared using chemical testing, FT-IR, GC and HPGPC. The results suggested that MM-P3 had higher molecular weights than MM-P1 and MM-P2. MM-P1 was consisted of glucose, MM-P2 was consisted of glucose and xylose, and MM-P3 was comprised of glucose, xylose and mannose. Differed from MM-P1 and MM-P2, MM-P3 had sulfuric radical and uronic acid groups. Finally, their antioxidant activities were also compared. We found that MM-P3 exhibited better antioxidant bioactivities than MM-P1 and MM-P2. The data demonstrated that three purified fractions derived from different adsorption capacity of DEAE-Sepharose fast-flow column possessed different structural characteristics and antioxidant activity.
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http://dx.doi.org/10.1016/j.ijbiomac.2017.12.023DOI Listing
March 2018

Catalytic asymmetric total synthesis of (S)-(-)-zearalenone, a novel lipoxygenase inhibitor.

Bioorg Med Chem 2013 Sep 20;21(17):5271-4. Epub 2013 Jun 20.

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.

A catalytic asymmetric synthesis of (S)-(-)-zearalenone is reported using asymmetric allylic alkylation for the introduction of the stereocenter. (S)-(-)-Zearalenone turned out to be a novel lipoxygenase inhibitor.
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http://dx.doi.org/10.1016/j.bmc.2013.06.024DOI Listing
September 2013

A novel catalytic asymmetric route towards skipped dienes with a methyl-substituted central stereogenic carbon.

Chem Commun (Camb) 2013 Apr;49(32):3309-11

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.

A highly efficient method for the enantioselective synthesis of 1,4-dienes (skipped dienes) with a methyl-substituted central stereogenic carbon using copper-catalysed asymmetric allylic alkylation of diene bromides was developed. Excellent regio- and enantioselectivity (up to 97 : 3 SN2'/SN2 ratio and 99% ee) were achieved with broad substrate scope.
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http://dx.doi.org/10.1039/c3cc41021hDOI Listing
April 2013

A concise asymmetric synthesis of (-)-rasfonin.

Org Biomol Chem 2012 Jan 24;10(1):29-31. Epub 2011 Nov 24.

Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.

A very efficient total synthesis of the apoptosis inducer (-)-rasfonin has been developed using CuBr/JosiPhos catalyzed iterative asymmetric conjugate addition of MeMgBr and Feringa's butenolide.
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http://dx.doi.org/10.1039/c1ob06700aDOI Listing
January 2012
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