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Preparation of benziodazole-triflate and its application as both 2-iodobenzamido-and triflate-transfer reagents
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作者 Yadong Li Feng-Huan Du +5 位作者 Junjie Li Jun Xu Zhifang Yang Shanshan Li Chi Zhang Yunfei Du 《Chinese Chemical Letters》 2025年第6期409-416,共8页
Benziodazole-triflate,as a novel heterocyclic hypervalent iodine(III)reagent,was prepared from the reaction of hypervalent chloroiodine(III)with silver triflate under mild conditions.The structure of this new reagent ... Benziodazole-triflate,as a novel heterocyclic hypervalent iodine(III)reagent,was prepared from the reaction of hypervalent chloroiodine(III)with silver triflate under mild conditions.The structure of this new reagent was elucidated by NMR spectroscopy and X-ray crystallography,and its reactions with diverseα-electron withdrawing group substituted carbonyl compounds were investigated.The results implied that benziodazole-triflate could be selectively used as both a 2-iodobenzamido-transfer reagent for the synthesis of oxazole compounds,and a triflate-transfer reagent for the triflation ofβ-keto-sulfones.Ionic mechanistic pathways,supported by density functional theory(DFT)calculations,were proposed to account for the divergent selectivities of the transformations. 展开更多
关键词 Benziodazole-triflate 2-Iodobenzamido-transfer reagent Oxidative cyclization Triflate-transfer reagent triflation Ionic mechanistic pathways
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Highly efficient and green synthesis of 14-aryl(alkyl)-14H-dibenzo[a,j]xanthene and 1,8-dioxooctahydroxanthene derivatives catalyzed by reusable zirconyl triflate[ZrO(OTf)_2]under solvent-free conditions 被引量:3
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作者 Iraj Mohammadpoor-Baltork Majid Moghadam +2 位作者 Valiollah Mirkhani Shahram Tangestaninejad Hamid Reza Tavakoli 《Chinese Chemical Letters》 SCIE CAS CSCD 2011年第1期9-12,共4页
An efficient, convenient and green method has been introduced for the preparation of 14-aryl(alkyl)-14H-dibenzo[a,j]xanthene and 1,8-dioxooctahydroxanthene derivatives by the reaction of aldehydes with 2-naphthol an... An efficient, convenient and green method has been introduced for the preparation of 14-aryl(alkyl)-14H-dibenzo[a,j]xanthene and 1,8-dioxooctahydroxanthene derivatives by the reaction of aldehydes with 2-naphthol and 5,5-dimethyl-1,3-cyclohexanedione, respectively, in the presence of ZrO(OTf)2 as a reusable catalyst under solvent-free conditions. In addition, very short reaction times, excellent yields, straightforward procedure, and relatively non-toxicity of the catalyst are other noteworthy advantages of the present method. 展开更多
关键词 XANTHENES Zirconyl triflate ALDEHYDES 2-NAPHTHOL Reusable catalyst
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4-(Benzylamino)formoyldiphenylammonium Triflate (BDPAT):An Efficient, Recoverable Biphasic Catalyst For Esterification of Carboxylic Acids with Equimolar Amounts of Alcohols 被引量:4
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作者 Ming LEI Cheng MA Yan Guang WANG 《Chinese Chemical Letters》 SCIE CAS CSCD 2002年第6期487-488,共2页
Esterification of carboxylic acid with equimolar amounts alcohol can be efficiently catalyzed by biphasic 4-(benzylamino)formoyldiphenylammonium triflate (BDPAT, 3) in good yield. The catalyst can be easily recovered... Esterification of carboxylic acid with equimolar amounts alcohol can be efficiently catalyzed by biphasic 4-(benzylamino)formoyldiphenylammonium triflate (BDPAT, 3) in good yield. The catalyst can be easily recovered without loss of activity. 展开更多
关键词 Benzylamino)formoyldiphenylammonium triflate biphasic catalyst esterification.
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A facile synthesis of 2,3-dihydro-2-aryl-4(1H)-quinazolinones catalyzed by scandium(Ⅲ) triflate 被引量:4
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作者 Jiu Xi Chen Hua Yue Wu Wei Ke Su 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第5期536-538,共3页
2,3-Dihydro-2-aryl-4(1H)-quinazolinones were prepared in good yields via condensation of o-aminobenzamide with aldehydes promoted by a catalytic amount of Sc(OTf)3 under mild conditions.
关键词 Scandium(Ⅲ) triflate 2 3-Dihydro-2-aryl-4(1H)-quinazolinones o-Aminobenzamide
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Highly efficient and easy synthesis of 2,4,6-triarylpyridines catalyzed by pentafluorophenylammonium triflate(PFPAT) as a new recyclable solid acid catalyst in solvent-free conditions 被引量:2
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作者 Naser Montazeri Saber Mahjoob 《Chinese Chemical Letters》 SCIE CAS CSCD 2012年第4期419-422,共4页
Pentafluorophenylammonium triflate(PFPAT) was found to be a highly efficient catalyst for the preparation of 2,4,6- triarylpyridines from the reaction of acetophenone derivatives,aromatic aldehydes and ammonium acet... Pentafluorophenylammonium triflate(PFPAT) was found to be a highly efficient catalyst for the preparation of 2,4,6- triarylpyridines from the reaction of acetophenone derivatives,aromatic aldehydes and ammonium acetate.Present methodology offers several advantages,such as short reaction time,high yields,simple procedure with an easy work-up and the absence of any volatile and hazardous organic solvent.In addition,this catalytic system can act as an active,inexpensive,metal-free,recoverable and recyclable catalyst. 展开更多
关键词 Pentafluorophenylammonium triflate 2 4 6-Triarylpyridines Solvent-free conditions ORGANOCATALYST Multi-component reaction
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Zirconium triflate grafted on SBA-15 as a highly efficient solid acid catalyst for ring opening of epoxides by amines and alcohols 被引量:2
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作者 Kamlesh N. Tayade Lianyue Wang +3 位作者 Sensen Shang Wen Dai Manish Mishra Shuang Gao 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 北大核心 2017年第4期758-766,共9页
Metal(Al,Ti,Zr)triflate grafted mesoporous SBA‐15(AlTf/S,TiTf/S,ZrTf/S)samples were synthesizedas inexpensive solid acid materials by a simple one‐pot‐two‐step synthesis methodology.These materials were characteri... Metal(Al,Ti,Zr)triflate grafted mesoporous SBA‐15(AlTf/S,TiTf/S,ZrTf/S)samples were synthesizedas inexpensive solid acid materials by a simple one‐pot‐two‐step synthesis methodology.These materials were characterized by X‐ray diffraction,N2‐sorption,thermogravimetric analysis,Fourier transform infrared spectroscopy(FT‐IR),in‐situ pyridine FT‐IR spectroscopy,and elementalanalysis.ZrTf/S was found to be a highly efficient and reusable solid acid catalyst for ring opening ofepoxides with amines and alcohols and producedβ‐amino alcohols andβ‐alkoxy alcohols respectivelyunder ambient reaction conditions.The ZrTf/S catalyst showed the highest activity,whichwas attributed to its high acidity compared with that of the Ti and Al containing samples. 展开更多
关键词 Epoxide ring opening Acid catalysis Metal triflate Grafted catalyst Mesoporous silica
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Morpholine triflate promoted one-pot,four-component synthesis of dihydropyrano[2,3-c]pyrazoles 被引量:3
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作者 Chen-Feng Zhou Jian-Jun Li Wei-Ke Su 《Chinese Chemical Letters》 SCIE CAS CSCD 2016年第11期1686-1690,共5页
A one-pot, four-component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile was discussed using Lewis acid catalyst morpholine triflate (MorT) to afford a series of dihydropyrano[2,3-c]... A one-pot, four-component reaction of ethyl acetoacetate, hydrazine hydrate, aldehydes, and malononitrile was discussed using Lewis acid catalyst morpholine triflate (MorT) to afford a series of dihydropyrano[2,3-c]pyrazoles, which were generally catalyzed by organic alkalis. Moderate to excellent yields, no chromatographic purification, and evasion of environmentally hazardous solvents in the reaction process make this protocol very useful for academia and industry. 展开更多
关键词 Dihydropyrano[2 3-c]pyrazole MCRs Morpholine triflate Green chemistry Lewis acid
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Rare earth metal triflates catalyzed electrophilic nitration using N_2O_5 被引量:8
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作者 Xiao Ming Ma Bin Dong Li +1 位作者 Ming Lu Chun Xu Lv 《Chinese Chemical Letters》 SCIE CAS CSCD 2012年第1期73-76,共4页
A mild,efficient and eco-friendly process for the electrophilic nitration is described using N_2O_5 as a green nitrating agent in the presence of rare earth metal triflates[RE(OTf)_3]under mild conditions.
关键词 Nitration Rare earth metal triflates N_2O_5 Catalysis
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Oxone-Mediated Oxidative Esterification of Heterocyclic Aldehydes Using Indium(III) Triflate 被引量:3
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作者 Tomoko Mineno Saki Yoshino Akira Ubukata 《Green and Sustainable Chemistry》 2014年第1期20-23,共4页
Recent investigations have shown the oxone-mediated oxidative methyl esterification of benzaldehyde derivatives using methanol. The reactions were accelerated in the presence of indium(III) triflate, a trivalent indiu... Recent investigations have shown the oxone-mediated oxidative methyl esterification of benzaldehyde derivatives using methanol. The reactions were accelerated in the presence of indium(III) triflate, a trivalent indium reagent, in many cases. Based on this method of methyl esterification of benzaldehyde derivatives, we further explored an application to heterocyclic aldehydes. The reactions were examined using methanol as well as other alcohols in order to establish a suitable range. 展开更多
关键词 Oxidative ESTERIFICATION HETEROCYCLIC ALDEHYDES Indium(III) TRIFLATE
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Generation of(E)-β-trifluoromethyl vinylsulfonohydrazides under photocatalysis and their anti-bacteria activity 被引量:1
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作者 Xinhua Wang Wei Zhou +2 位作者 Wenlin Xie Qi Chen Jie Wu 《Chinese Chemical Letters》 SCIE CAS CSCD 2023年第6期350-353,共4页
Trifluoromethylation/sulfonylation of alkynes from trifluoromethyl thianthrenium triflate and sulfur dioxide under extremely mild reaction conditions provides a facile access to trifluoromethyl-substituted vinyl sulfo... Trifluoromethylation/sulfonylation of alkynes from trifluoromethyl thianthrenium triflate and sulfur dioxide under extremely mild reaction conditions provides a facile access to trifluoromethyl-substituted vinyl sulfonohydrazides in moderate to good yields.This multicomponent reaction of trifluoromethyl thianthrenium triflate,alkynes,sulfur dioxide and hydrazines proceeds efficiently under visible light irradiation in the presence of photocatalyst at room temperature with broad substrate scope and excellent functional group compatibility.This reaction is highly stereoselective,and only(E)-isomers are obtained.Additionally,these trifluoromethyl-substituted vinyl sulfonohydrazides are further evaluated for anti-bacteria activity.In vitro activities of these compounds against Staphylococcus aureus(G+)and Escherichia coli(G-)are examined. 展开更多
关键词 ALKYNE HYDRAZINE PHOTOCATALYSIS Sulfur dioxide Trifluoromethyl thianthrenium triflate
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Silica triflate as an efficient reagent for the solvent-free synthesis of coumarins 被引量:1
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作者 Farhad Shirini Katayoun Marjani +1 位作者 Hossein Taherpour Nahzomi Mohammad Ali Zolfigol 《Chinese Chemical Letters》 SCIE CAS CSCD 2007年第8期909-911,共3页
Silica triflate, as a new silica-based reagent, can be used for the efficient synthesis of 4-substituted coumarins via a Pechmann reaction under solvent-free reaction conditions. All reactions were performed at 80 ℃ ... Silica triflate, as a new silica-based reagent, can be used for the efficient synthesis of 4-substituted coumarins via a Pechmann reaction under solvent-free reaction conditions. All reactions were performed at 80 ℃ in good to high yields. 展开更多
关键词 Silica triflate COUMARINS Pechmann reaction Solvent-free reaction conditions PHENOLS
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Aluminum(Ⅲ) triflate-catalyzed selective oxidation of glycerol to formic acid with hydrogen peroxide 被引量:1
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作者 Kang Kong Difan Li +3 位作者 Wenbao Ma Qingqing Zhou Guoping Tang Zhenshan Hou 《Chinese Journal of Catalysis》 SCIE EI CAS CSCD 北大核心 2019年第4期534-542,M0003,共10页
Glycerol is a by-product of biodiesel production and is an important readily available platform chemical.Valorization of glycerol into value-added chemicals has gained immense attention.Herein,we carried out the conve... Glycerol is a by-product of biodiesel production and is an important readily available platform chemical.Valorization of glycerol into value-added chemicals has gained immense attention.Herein,we carried out the conversion of glycerol to formic acid and glycolic acid using H2O2 as an oxidant and metal(Ⅲ)triflate-based catalytic systems.Aluminum(Ⅲ)triflate was found to be the most efficient catalyst for the selective oxidation of glycerol to formic acid.A correlation between the catalytic activity of the metal cations and their hydrolysis constants(Kh)and water exchange rate constants was observed.At 70 ℃,a formic acid yield of up to 72% could be attained within 12 h.The catalyst could be recycled at least five times with a high conversion rate,and hence can also be used for the selective oxidation of other biomass platform molecules.Reaction kinetics and 1H NMR studies showed that the oxidation of glycerol(to formic acid)involved glycerol hydrolysis pathways with glyceric acid and glycolic acid as the main intermediate products.Both the [Al(OH)x]^n+ Lewis acid species and CF3SO3H Brosted acid,which were generated by the in-situ hydrolysis of Al(OTf)3,were responsible for glycerol conversion.The easy availability,high efficiency,and good recyclability of Al(OTf)3 render it suitable for the selective oxidation of glycerol to high value-added products. 展开更多
关键词 Aluminum(Ⅲ)triflate GLYCEROL Hydrogen peroxide Selective oxidation Formic acid
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A Novel Initiator Containing Alkyne Group for the Polymerization of 2-Ethyl-2-oxazoline
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作者 Muhammad Waqas Ali 高亚婷 +1 位作者 Muhammad Siddiq 叶晓东 《Chinese Journal of Chemical Physics》 SCIE CAS CSCD 2018年第1期77-84,I0002,共9页
A novel trifunctional initiator with one alkyne and two trifluoromethanesulfonate moieties was synthesized from a protected alcohol 5-hydroxyl-2-phenyl-1, 3-dioxane. The alkyne func- tionalized intermediate with two p... A novel trifunctional initiator with one alkyne and two trifluoromethanesulfonate moieties was synthesized from a protected alcohol 5-hydroxyl-2-phenyl-1, 3-dioxane. The alkyne func- tionalized intermediate with two protected alcohol groups was synthesized by reacting with propargyl bromide. The alcohol groups were cleaved using a mixture of tetrahydrofuran and hydrochloric acid aqueous solution. In the last step the initiator was synthesized us- ing triflic anhydride in carbon tetrachloride. The initiator was characterized by 1H NMR and used for the polymerization of 2-ethyl-2-oxazoline which gives polymers with narrow distribution. For comparison a similar initiator with two tosylates was prepared and used for the polymerization of the monomer 2-ethyl-2-oxazoline, the resulting product has a wide molecular weight distribution and most of the initiator remains unreacted after 24 h which may be due to the steric hindrance between the two tosylate groups. To further explore the steric hindrance phenomenon, a linear tosylate initiator was synthesized, but still some of the initiator remains unreacted, illustrating that both steric hindrance and electrophilic balance affect the efficiency of the cationic ring-opening polymerization. All of the polymers were characterized in detail by using IH NMR, matrix-assisted laser desorption/ionization time-of-flight mass spectroscopy, and size exclusion chromatography to confirm the purity and distribution of the polymers. 展开更多
关键词 ELECTROPHILE 2-Ethyl-2-oxazoline Steric hindrance TRIFLATE
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Highly-Efficient Conversion of Primary Amides to Nitriles Using Indium(III) Triflate as the Catalyst 被引量:2
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作者 Tomoko Mineno Mamika Shinada +3 位作者 Kazuki Watanabe Hitoshi Yoshimitsu Hiroyuki Miyashita Hisao Kansui 《International Journal of Organic Chemistry》 2014年第1期1-6,共6页
Indium(III) triflate, a trivalent indium reagent, was shown to be a highly-efficient catalyst for the conversion of primary amides to the corresponding nitriles. The successful reactions required 5 mol% of indium(III)... Indium(III) triflate, a trivalent indium reagent, was shown to be a highly-efficient catalyst for the conversion of primary amides to the corresponding nitriles. The successful reactions required 5 mol% of indium(III) triflate, and toluene was proved to be the most suitable solvent. Various amides were subjected to this method, and each produced the corresponding nitriles in excellent yields. 展开更多
关键词 Indium(III) TRIFLATE PRIMARY AMIDES NITRILES
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Facile and Efficient Method for Synthesis of Benzimidazole Derivatives Catalyzed by Zinc Triflate 被引量:1
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作者 Ramineni Srinivasulu Kannasani Ravi Kumar Peruri Veera Venkata Satyanarayana 《Green and Sustainable Chemistry》 2014年第1期33-37,共5页
We report the synthesis of benzimidazole derivatives using zinc triflate as an efficient catalyst. One-pot synthesis of 2-substituted benzimidazole derivatives from o-phynelyenediamine and substituted aldehydes were d... We report the synthesis of benzimidazole derivatives using zinc triflate as an efficient catalyst. One-pot synthesis of 2-substituted benzimidazole derivatives from o-phynelyenediamine and substituted aldehydes were developed under zinc triflate in ethanol solvent at reflux temperature. 展开更多
关键词 BENZIMIDAZOLE Derivatives O-Phynelyenediamine SUBSTITUTED ALDEHYDES Zinc TRIFLATE
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Effect of Added Cu(OTf)<sub>2</sub>on the Cu(OTf)<sub>2</sub>(Py)<sub>4</sub>-Mediated Radiofluorination of Benzoyl and Phthaloylglycinates 被引量:1
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作者 David W. Blevins George W. Kabalka +1 位作者 Dustin R. Osborne Murthy R. Akula 《Natural Science》 2018年第3期125-133,共9页
Cu(OTf)2(Py)4 mediated radiofluorination of the boronate esters of ethyl benzoyl and phthaloylglycinates (11 and 16) using 10 mol% of the copper complex following the literature procedure did not provide the fluorinat... Cu(OTf)2(Py)4 mediated radiofluorination of the boronate esters of ethyl benzoyl and phthaloylglycinates (11 and 16) using 10 mol% of the copper complex following the literature procedure did not provide the fluorinated products. However, the addition of Cu(OTf)2resulted in the radio-fluorination of the boronate esters 11 and 16 to obtain ethyl 4-[18F]fluorobenzoyl glycinate, 17, (48%) and ethyl 3-[18F]phthaloylglycinate (41%) respectively. 展开更多
关键词 Glycinates BORONATE Esters Gorlos-Phos RADIOFLUORINATION Copper Triflate
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L-ProT catalyzed highly regioselective N-alkoxyalkylation of purine rings with vinyl ethers 被引量:1
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作者 Jian-Jun Li Xing-Xing Gui 《Chinese Chemical Letters》 SCIE CAS CSCD 2014年第10期1341-1345,共5页
An efficient and regioselective synthesis of N-9 alkoxyalkylated purine nucleoside derivatives was achieved via the N-alkoxyalkylation of purine rings with vinyl ethers catalyzed by L-ProT.The advantages of this proto... An efficient and regioselective synthesis of N-9 alkoxyalkylated purine nucleoside derivatives was achieved via the N-alkoxyalkylation of purine rings with vinyl ethers catalyzed by L-ProT.The advantages of this protocol include good to excellent yield,mild reaction condition,and simple manipulation.A plausible mechanism for the transformation was given. 展开更多
关键词 L-Proline triflate Regioselectivity Purine Vinyl ether Addition reaction
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Oxone-Mediated Preparation of Ester Derivatives Using Indium(III) Triflate and Various Alcohols 被引量:1
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作者 Tomoko Mineno Daiki Takano +2 位作者 Saika Komiya Azusa Sato Hisao Kansui 《Green and Sustainable Chemistry》 2022年第1期1-8,共8页
Esters are known as one of the most fundamental chemical moieties and also essentially useful components, especially for medicinal agents. Herein, using benzaldehyde and its derivatives as starting materials, Oxone-me... Esters are known as one of the most fundamental chemical moieties and also essentially useful components, especially for medicinal agents. Herein, using benzaldehyde and its derivatives as starting materials, Oxone-mediated preparation of ester derivatives in the presence of a catalytic amount of indium(III) triflate is described. Alcohols with various chain lengths, which functioned as solvents and substrates, were examined. Overall, the oxidative esterification starting with benzaldehyde derivatives possessing electron withdrawing groups proceeded smoothly and gave sufficient yields, in comparison to the reactions with the derivatives having electron donating groups. 展开更多
关键词 OXONE Oxidative Esterification Benzaldehyde Derivatives Ester Derivatives Indium(III) Triflate ALCOHOLS
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Nitroxide-Mediated Photo-Controlled/Living Radical Polymerization of Methacrylic Acid 被引量:1
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作者 Eri Yoshida 《Open Journal of Polymer Chemistry》 2013年第1期16-22,共7页
The photo-controlled/living radical polymerization of methacrylic acid (MAA) was performed at room temperature by irradiation with a high-pressure mercury lamp using azo initiators and 4-methoxy-2,2,6,6-tetramethylpip... The photo-controlled/living radical polymerization of methacrylic acid (MAA) was performed at room temperature by irradiation with a high-pressure mercury lamp using azo initiators and 4-methoxy-2,2,6,6-tetramethylpiperidine-1-oxyl as the mediator in the presence of (4-tert-butylphenyl)diphenylsulfonium triflate (tBuS) as the accelerator. Whereas the bulk polymerization yielded polymers with a bimodal molecular weight distribution in both the absence and presence of tBuS, the solution polymerization in methanol produced unimodal polymers with the molecular weight distribution of 2.0 - 2.3 in the presence of tBuS. The molecular weight distribution of the resulting poly (MAA) decreased with an in- crease in tBuS. The dilution of the monomer concentration also reduced the molecular weight distribution. The use of the initiator with a low 10-h half-life temperature also effectively controlled the molecular weight. The livingness of the polymerization was confirmed by obtaining linear increases in the first-order conversion versus time, the molecular weight versus the conversion, and the molecular weight versus the reciprocal of the initiator concentration. 展开更多
关键词 Photo-Controlled/Living Radical POLYMERIZATION Nitroxide-Mediated POLYMERIZATION Methacrylic Acid 4-Methoxy-2 2 6 6-Tetramethylpiperidine-1-Oxyl (4-Tert-butylphenyl)diphenylsulfonium TRIFLATE Molecular Weight Control
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A one-pot protocol for copper-mediated azide–alkyne cycloaddition using alkenyl triflate precursors
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作者 Yu Chen Lianchao Liu +2 位作者 Dimin Wu Yu-Peng He Ang Li 《Chinese Chemical Letters》 SCIE CAS CSCD 2019年第1期269-270,共2页
On the basis of the mild transformation of alkenyl triflates into alkynes promoted by LiCl, a one-pot protocol using alkenyl triflate precursors was developed for copper-mediated azide–alkyne cycloaddition. This prot... On the basis of the mild transformation of alkenyl triflates into alkynes promoted by LiCl, a one-pot protocol using alkenyl triflate precursors was developed for copper-mediated azide–alkyne cycloaddition. This protocol may provide an opportunity of sequentially click reactions for the construction of bifunctional probes in chemical biology studies. 展开更多
关键词 Click chemistry Azide-alkyne CYCLOADDITION ALKENYL TRIFLATES Lithium chloride
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