- Diethylammonium iodide as catalyst for the metal-free synthesis of 5-aryl-2-oxazolidinones from aziridines and carbon dioxide
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The catalytic potential of ammonium halide salts was explored in the coupling reaction of a model aziridine with carbon dioxide, highlighting the superior activity of [NH2Et2]I. Then, working at room temperature, atmospheric CO2 pressure and in the absenc
- Bresciani, Giulio,Bortoluzzi, Marco,Pampaloni, Guido,Marchetti, Fabio
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p. 4152 - 4161
(2021/05/19)
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- Efficient Cycloaddition of CO2and Aziridines Activated by a Quadruple-Interpenetrated Indium-Organic Framework as a Recyclable Catalyst
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On the basis of the global warming effect, it is of great significance to convert CO2 into the high value-added products oxazolidinones, but investigations on main-group-based metal-organic frameworks (MOFs) as heterogeneous catalysts still have not been
- Tian, Xue-Rui,Shi, Ying,Hou, Sheng-Li,Ma, Yue,Zhao, Bin
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supporting information
p. 15383 - 15389
(2021/10/20)
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- Diastereoselective Construction of Cyclopropane-Fused Tetrahydroquinolines via a Sequential [4 + 2]/[2 + 1] Annulation Reaction
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A sequential [4 + 2]/[2 + 1] annulation of α-aryl vinylsulfoniums with 2-aminochalcones and 2-(2-aminobenzylidene)-1H-indene-1,3(2H)-dione is reported that affords a series of cyclopropane-fused tetrahydroquinolines. The salient features of this novel and practical transformation include high efficiency, transition-metal-free nature, operational simplicity, and outstanding functional group tolerance.
- Wang, Zhen-Hua,Shen, Li-Wen,Xie, Ke-Xin,You, Yong,Zhao, Jian-Qiang,Yuan, Wei-Cheng
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supporting information
p. 3114 - 3118
(2020/04/20)
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- Iodine-Catalyzed Ring Opening of 1,1-Diacylcyclopropanes for Synthesis of Fully Substituted Pyrazole Derivatives
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An iodine-catalyzed [3+2] cycloaddition/ring opening reaction of 1,1-diacylcyclopropanes with sulfonyl hydrazides has been reported. In the presence of 20 mol-% iodine, a range of structurally diverse fully substituted pyrazoles with a hydroxy functional group are obtained in moderate to excellent yields with extremely high regioselectivity.
- Bao, Yishu,Chen, Ming,Ding, Ziyu,Yang, Fulai,Yang, Xiuqin,Zhou, Qingfa,Zhu, Jin
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supporting information
(2020/07/04)
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- A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution
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A facile microwave assisted three-component protocol allows the synthesis of chiral aryl-1,2-mercaptoamines in water in a few minutes with high yields, bypassing the use of toxic aziridine intermediates. The chiral 1,2-mercaptoamines were then deracemized through enzymatic resolution of the racemates using monoamine oxidase (MAO-N) biocatalysts.
- Lauder, Kate,Masci, Domiziana,Toscani, Anita,Al Mekdad, Aya,Black, Gary W.,Brown, Nicola L.,Turner, Nicholas J.,Luisi, Renzo,Castagnolo, Daniele
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supporting information
p. 8982 - 8986
(2019/10/28)
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- Two Stable Heterometal-MOFs as Highly Efficient and Recyclable Catalysts in the CO2 Coupling Reaction with Aziridines
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Two stable heterometal-organic frameworks, {Na[LnCo(DATP)2(Ac)(H2O)](NO3)?DMA?11 H2O}n (Ln=Er(1) and Yb(2)), have been prepared with H2DATP (4′-(3,5-dicarboxyphenyl)-2,2′:6′,2′′′-terpyridin
- Kang, Xiao-Min,Yao, Lin-Hong,Jiao, Zhuo-Hao,Zhao, Bin
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supporting information
p. 3668 - 3674
(2019/08/01)
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- Chiral N,N′-Dioxide/ScΙΙΙ Complex-Catalyzed Asymmetric Ring-Opening Reaction of Cyclopropyl Ketones with Indoles
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The asymmetric ring-opening reaction of cyclopropyl ketones with indoles has been realized by using a N,N′-dioxide/scandium(ΙΙΙ) complex as catalyst. The corresponding 3-alkylated indole derivatives were obtained in moderate to excellent yields with good ee values. Moreover, a possible transition state was proposed on the basis of experimental studies and X-ray structure of product. (Figure presented.).
- Chang, Fenzhen,Lin, Lili,Xia, Yong,Zhang, Hang,Dong, Shunxi,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 2608 - 2612
(2018/05/30)
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- A multifunctional MOF as a recyclable catalyst for the fixation of CO2 with aziridines or epoxides and as a luminescent probe of Cr(VI)
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A multifunctional metal-organic framework (1) containing 24-nuclear zinc nanocages shows high solvent- and pH-stability. Compound 1 can be employed as a catalyst for the conversion of CO2 with aziridines or epoxides, which can be reused at leas
- Cao, Chun-Shuai,Shi, Ying,Xu, Hang,Zhao, Bin
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supporting information
p. 4545 - 4553
(2018/04/02)
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- Catalytic asymmetric [3 + 3] annulation of cyclopropanes with mercaptoacetaldehyde
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A highly diastereo- and enantioselective [3 + 3] annulation of donor-acceptor cyclopropanes with mercaptoacetaldehyde has been developed. In the presence of a N,N′-dioxide-Sc(iii) complex as the catalyst, a number of aromatic substituted cyclopropyl ketones reacted with mercaptoacetaldehyde smoothly, providing the corresponding chiral tetrahydrothiopyranols in moderate yields with excellent ee (up to 99% ee) and dr values (up to >19:1).
- Fu, Xuan,Lin, Lili,Xia, Yong,Zhou, Pengfei,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 5914 - 5917
(2016/07/06)
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- Asymmetric Ring Opening/Cyclization/Retro-Mannich Reaction of Cyclopropyl Ketones with Aryl 1,2-Diamines for the Synthesis of Benzimidazole Derivatives
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A highly efficient asymmetric ring-opening/cyclization/retro-Mannich reaction of cyclopropyl ketones with aryl 1,2-diamines has been realized using a chiral N,N′-dioxide/ScIIIcatalyst. Benzimidazoles containing chiral side chains were generated under mild reaction conditions in excellent outcomes (up to 99 % yield and 97 % ee). This method also provides efficient access to chiral benzimidazole-substituted amide and cycloheptene derivatives.
- Xia, Yong,Lin, Lili,Chang, Fenzhen,Liao, Yuting,Liu, Xiaohua,Feng, Xiaoming
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p. 12228 - 12232
(2016/10/13)
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- Asymmetric synthesis of 2,3-dihydropyrroles by ring-opening/ cyclization of cyclopropyl ketones using primary amines
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The asymmetric ring-opening/cyclization of cyclopropyl ketones with primary amine nucleophiles was catalyzed by a chiral N,N'-dioxide/scandium(III) complex through a kinetic resolution process. A broad range of cyclopropyl ketones and primary amines are suitable substrates of this reaction. The corresponding products were afforded in excellent enantioselectivities and yields (up to 97% ee and 98% yield) under mild reaction conditions. This method provides a promising access to chiral 2,3-dihydropyrroles as well as an effective procedure for the kinetic resolution of 2-substituted cyclopropyl ketones.
- Xia, Yong,Liu, Xiaohua,Zheng, Haifeng,Lin, Lili,Feng, Xiaoming
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supporting information
p. 227 - 230
(2015/02/05)
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- Asymmetric Ring-Opening of Cyclopropyl Ketones with Thiol, Alcohol, and Carboxylic Acid Nucleophiles Catalyzed by a Chiral N,N′-Dioxide-Scandium(III) Complex
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A highly efficient asymmetric ring-opening reaction of cyclopropyl ketones with a broad range of thiols, alcohols and carboxylic acids has been first realized by using a chiral N,N′-dioxide-scandium(III) complex as catalyst. The corresponding sulfides, ethers, and esters were obtained in up to 99 % yield and 95 % ee. This is also the first example of one catalytic system working for the ring-opening reaction of donor-acceptor cyclopropanes with three different nucleophiles, let alone in an asymmetric version.
- Xia, Yong,Lin, Lili,Chang, Fenzhen,Fu, Xuan,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 13748 - 13752
(2015/11/11)
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- Preparation of polystyrene-supported Lewis acidic Fe(III) ionic liquid and its application in catalytic conversion of carbon dioxide
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A polystyrene-supported Lewis acidic iron-containing ionic liquid was proved to be recyclable and efficient heterogeneous catalyst for converting CO2 into cyclic carbonate without utilization of any organic solvent or additive. Excellent yields and selectivity were obtained under mild reaction conditions. Notably, the catalyst could be readily recovered and reused over five times without appreciable loss of catalytic activity. A possible catalytic cycle was proposed. The present protocol has successfully been applied to reactions of aziridines/propargyl amines with CO2. This kind of the catalyst presented herein would have great potential in industrial application thanks to its featured advantages.
- Gao, Jian,Song, Qing-Wen,He, Liang-Nian,Liu, Chang,Yang, Zhen-Zhen,Han, Xu,Li, Xue-Dong,Song, Qing-Chuan
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supporting information; experimental part
p. 3835 - 3842
(2012/07/13)
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- Proline-catalyzed synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions
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Natural a-amino acids were proven to be ecofriendly and recyclable catalysts for the carboxylation of aziridines with CO2 without utilization of any organic solvents or additives. Notably, a series of 5-aryl-2-oxazolidinones were obtained in go
- Dou, Xiao-Yong,He, Liang-Nian,Yang, Zhen-Zhen
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experimental part
p. 62 - 74
(2011/11/05)
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- Polystyrene-supported amino acids as efficient catalyst for chemical fixation of carbon dioxide
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Four new polystyrene-supported amino acids have been synthesized and applied to the chemical fixation of carbon dioxide for the first time. Two series of experiments with polystyrene-supported threonine (PS-Thr) and polystyrene-supported tyrosine (PS-Tyr) as catalyst, respectively, were conducted to study the effect of the reaction conditions on the carboxylation of propylene oxide/carbon dioxide. There was no considerable decrease in the yield of propylene carbonate after the polystyrene-supported amino acids were used five times, indicating that these catalysts are very stable. It was demonstrated that these catalysts were very efficient in the carboxylation of various epoxides and aziridines with carbon dioxide under mild conditions without any solvents. The mechanism for this carboxylation is also discussed.
- Qi, Chaorong,Ye, Jinwu,Zeng, Wei,Jiang, Huanfeng
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supporting information; experimental part
p. 1925 - 1933
(2010/11/04)
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- Lewis basic ionic liquids-catalyzed synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 under solvent-free conditions
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A series of easily prepared Lewis basic ionic liquids were developed as recyclable and efficient catalysts for selective synthesis of 5-aryl-2-oxazolidinones from aziridines and CO2 without utilization of any organic solvent or additive. Notably, high conversion, chemo- and regio-selectivity were attained when 1-butyl-4-aza-1-azaniabicyclo[2.2.2]octane bromide ([C4DABCO]Br) was used as the catalyst. Furthermore, the catalyst could be recycled over four times without appreciable loss of catalytic activity. The effects of the catalyst structure and various reaction parameters on the catalytic performance were investigated in detail. This protocol was found to be applicable to a variety of aziridines producing the corresponding 5-aryl-2-oxazolidinones in good yields and excellent regioselectivities. Therefore, this solvent-free process thus represents an environmentally friendly process for ionic liquid-catalyzed conversion of CO2 into value-added chemicals. A possible catalytic cycle for CO2 activation induced by nucleophilic tertiary nitrogen of the ionic liquid was proposed, based on studies using in situ FT-IR spectroscopy under CO2 pressure.
- Yang, Zhen-Zhen,He, Liang-Nian,Peng, Shi-Yong,Liu, An-Hua
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supporting information; experimental part
p. 1850 - 1854
(2011/02/23)
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- Quaternary ammonium bromide functionalized polyethylene glycol: A highly efficient and recyclable catalyst for selective synthesis of 5-aryl-2-oxazolidinones from carbon dioxide and aziridines under solvent-free conditions
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(Chemical Equation Presented) A quaternary ammonium bromide covalently bound to polyethylene glycol (PEG, MW = 6000), i.e., PEG6000- (NBu3Br)2, was found to be an efficient and recyclable catalyst for the cycloaddition reaction of aziridines to CO2 under mild conditions without utilization of additional organic solvents or cocatalysts. As a result, 5-aryl-2-oxazolidinone was obtained in high yield with excellent regioselectivity. The catalyst worked well for a wide variety of 1-alkyl-2-arylaziridines. Besides, the catalyst could be recovered by centrifugation and reused without significant loss of catalytic activity and selectivity.
- Du, Ya,Wu, Ying,Liu, An-Hua,He, Liang-Nian
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p. 4709 - 4712
(2008/09/21)
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