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1. Synthesis, Characterization, and Spectroscopic Properties of a Phthalocyanine-Chlorambucil Conjugate | |||
Xiao-Hui Peng,Shao-Fang Chen,Mei-Rong Ke,Jian-Dong Huang | |||
Chemistry 05 January 2016 | |||
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Abstract:A novel zinc(II) phthalocyanine-chlorambucil conjugate (7) has been synthesized by treating an amino-mono-substituted zinc(II) phthalocyanine with chlorambucil, followed by characterization with 1H NMR and HRMS. Its photophyscial and photochemical properties has been investigated. The results indicate that it remains in the form of monoer and show a relative high singlet oxygen quantum yield in DMF, but exhibits a aggregation trend with a weaker and broadened Q band in aqueous solution ( PBS with 0.1% Cremophor EL), which also caused the reduction of fluorescence emission. In addition, after conjugating with chlorambucil, the generation of singlet oxygen of phthalocyanine decreased. | |||
TO cite this article:Xiao-Hui Peng,Shao-Fang Chen,Mei-Rong Ke, et al. Synthesis, Characterization, and Spectroscopic Properties of a Phthalocyanine-Chlorambucil Conjugate[OL].[ 5 January 2016] http://en.paper.edu.cn/en_releasepaper/content/4674815 |
2. Rhodium(III)-Catalyzed C-H/C-C Coupling of Benzamides with 2-Vinylcyclopropane-1,1-dicarboxylate | |||
GUO Yuntao,WANG Baiquan | |||
Chemistry 14 December 2015 | |||
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Abstract:2-Vinylcyclopropane-1,1-dicarboxylate was used as a building block to react with benzamides in rhodium(III)-catalyzed amide-directed selective C-H/C-C coupling reactions. The reactions are accompanied the ring-opening of the cyclopropane and a new type of allylated arenes were obtained A wide variety of functional groups are tolerated with good to high yields. Furthermore, further transformations of the coupled products have been performed. The decarboxylation product and alkylation products were obatined in high yields. Hydrogenation with Pd/C as catalyst could transform the E/Z mixtures of 3 to the corresponding single saturated products 7 in 87-92 yields. This catalytic system expanded the synthetic utility of rhodium(III)-catalyzed C-H activation. | |||
TO cite this article:GUO Yuntao,WANG Baiquan. Rhodium(III)-Catalyzed C-H/C-C Coupling of Benzamides with 2-Vinylcyclopropane-1,1-dicarboxylate[OL].[14 December 2015] http://en.paper.edu.cn/en_releasepaper/content/4670675 |
3. Synthesis, structures, and norbornene polymerization behavior of palladium methyl complexes bearing N-heterocyclic carbene-sulfonate ligands | |||
LI Minliang,WANG Baiquan | |||
Chemistry 14 December 2015 | |||
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Abstract:A series of N-heterocyclic carbene-sulfonate (NHC-sulfonate) palladium methyl complexes 2a-d were synthesized from the reaction of NHC-sulfonate ligands with Ag2O and Pd2(μ-Cl)2Me2(2,6-lutidine)2 in good yields. All these complexes were fully characterized by 1H and 13C NMR, elemental analysis, and high-resolution mass spectrometry (HRMS). The molecular structure of the representative complex 2a was also determined by single-crystal X-ray diffraction analysis. Upon activation with either methylaluminoxane (MAO) or [Ph3C]+[B(C6F5)4]-, all the palladium methyl complexes showed excellent catalytic activities [up to 108 g of polynorbornene (PNB) (mol of Pd)-1 h-1] in the vinyl polymerization of norbornene. | |||
TO cite this article:LI Minliang,WANG Baiquan. Synthesis, structures, and norbornene polymerization behavior of palladium methyl complexes bearing N-heterocyclic carbene-sulfonate ligands[OL].[14 December 2015] http://en.paper.edu.cn/en_releasepaper/content/4670742 |
4. Unexpected Solvent Effects in Controlling Stereoselectivity and Product Distribution: Catalyst-free Reaction of Propranolol with (S)-2-acetoxy-succinic Acid Divinyl Ester | |||
ZHANG Qingyi,LIN Xianfu | |||
Chemistry 03 December 2015 | |||
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Abstract:The stereoselectivity and product distribution of catalyst-free reaction of propranolol with (S)-2-acetoxy-succinic acid divinyl ester are shown to be solvent-dependent. In moderate polar solvents, propranolol undergo regioselective acylation and (R)-propranolol vinyl ester spontaneously cyclize, so as to provide the remained (S)-propranolol vinyl ester with high 97% de value. The intramolecular hydrogen bond between the carbonyl group and the propranolol's hydroxy functionality affects the cyclization activity of (R)- or (S)-propranolol vinyl ester in different solvents. However, strong polar solvent are favorable for the cyclization of both (R)- and (S)-propranolol vinyl ester. Distribution of obtained six- or seven-membered morpholinone derivatives was dependent on the nature of the solvent. The best result was the selective formation of 3-morpholinone derivatives in 96% yields. A tandem process of transesterification and β-elimination/Michael addition is a tentative mechanism basing on some designed experiments. | |||
TO cite this article:ZHANG Qingyi,LIN Xianfu. Unexpected Solvent Effects in Controlling Stereoselectivity and Product Distribution: Catalyst-free Reaction of Propranolol with (S)-2-acetoxy-succinic Acid Divinyl Ester[OL].[ 3 December 2015] http://en.paper.edu.cn/en_releasepaper/content/4667116 |
5. Comparative Studies of Three Synthetic Routes of Enzymatic Multicomponent Reactions (MCRs) for Strongly Fluorescent Spirooxazino Derivatives | |||
CHEN Xiaoyang,LIN Xianfu | |||
Chemistry 03 December 2015 | |||
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Abstract:Enzymatic multicomponent reactions are very powerful for complicated organic synthesis with environmental friendly, highly efficient and selective characters. Herein, we designed and compared three routes of enzymatic MCRs for simple and efficient synthesis of complicated spirooxazinos derivatives, and one more efficient synthesis methodology for the target compounds than before was developed. Reaction conditions such as enzymes, enzyme concentration, amides and ratio of substrates were screened, and 15 spirooxazino derivatives were obtained in moderate to good yield. All of these novel spirooxazinos have strong fluorescence emission ability and high quantum yields, providing great application potential in photoactive materials. Furthermore, particularly interesting is that chiral spirooxazino could also be obtained through a developed two-enzymatic MCRs process in one pot. | |||
TO cite this article:CHEN Xiaoyang,LIN Xianfu. Comparative Studies of Three Synthetic Routes of Enzymatic Multicomponent Reactions (MCRs) for Strongly Fluorescent Spirooxazino Derivatives[OL].[ 3 December 2015] http://en.paper.edu.cn/en_releasepaper/content/4666965 |
6. Mechanistic Studies of Rh(III)-Catalyzed C-H Olefination of Pyridines and Quinolines Promoted by Cu(OAc)2 | |||
ZHOU Jun,ZHANG Shuo-Qing,LI Bo,SHI Bing-Feng | |||
Chemistry 01 December 2015 | |||
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Abstract:Detailed investigations towards the mechanistic studies of our previous work on Rh(III)-catalyzed C-H olefination of pyridines and quinolines are reported here. A working hypothesis was proposed for based on experimental and computional studies. The key reaction intermediate 11a was isolated and determined by X-ray crystallography, displaying a dimeric copper coordinated at the pyridine nitrogen. The KIE studies indicates that the cleavage of the C-H bond was not involved in the rate-determining step. The DFT calculations show the orientation of -CO- benefits its function as a directing group and promoted the following reaction. In addtion, controlled experiments have also been conducted. These studies indicate that Cu(OAc)2 might serve as both a convenient oxidant and Lewis acid. | |||
TO cite this article:ZHOU Jun,ZHANG Shuo-Qing,LI Bo, et al. Mechanistic Studies of Rh(III)-Catalyzed C-H Olefination of Pyridines and Quinolines Promoted by Cu(OAc)2[OL].[ 1 December 2015] http://en.paper.edu.cn/en_releasepaper/content/4665182 |
7. Enantioselective Synthesis of Polysubstituted Tetrahydroquinolines via an Organocatalytic Asymmetric Cascade Reaction | |||
LUO Yongchun,HAN Ronggang,XU Pengfei | |||
Chemistry 27 November 2015 | |||
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Abstract:Based on the principles of organocatalysis. An enantioselective and efficient catalytic method for synthesis of polysubstituted tetrahydroquinolines via an aldol/nucleophilic addition cascade reaction was developed. This domino process affords a series of tetrahydroquinoline products with good yields (up to 89%) and high diastereo- and enantiocontrol (dr up to >25:1, ee up to 97%). The structre of the products was characterized by NMR, IR, HR Ms and X-ray differaction. In addition, using some simple reactions, the product structure can be easily modified. | |||
TO cite this article:LUO Yongchun,HAN Ronggang,XU Pengfei. Enantioselective Synthesis of Polysubstituted Tetrahydroquinolines via an Organocatalytic Asymmetric Cascade Reaction[OL].[27 November 2015] http://en.paper.edu.cn/en_releasepaper/content/4665107 |
8. Intermolecular 1,3-Dipolar Cycloaddition Reactions of Chiral Cyclic Nitrones with Alkenes | |||
LUO Yongchun,CHENG Ruiling,XU Pengfei | |||
Chemistry 27 November 2015 | |||
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Abstract:A efficient 1,3-dipolar cycloaddition reaction between the new chiral cyclic nitrones and alkenes was studied. After the optimization of reaction conditions, a series of valuable chiral isoxazolidine products were prepared with high yields. The structre of the products was characterized by NMR, IR and HR Ms. In addition, according to the analysis of the reaction's transition state, the stereoselevtivity of this cycloaddition and the absolute configuration of cycloadducts was explained reasonably. | |||
TO cite this article:LUO Yongchun,CHENG Ruiling,XU Pengfei. Intermolecular 1,3-Dipolar Cycloaddition Reactions of Chiral Cyclic Nitrones with Alkenes[OL].[27 November 2015] http://en.paper.edu.cn/en_releasepaper/content/4665101 |
9. Synthesis and photophysical properties of star-shaped fluorescent molecules composed of 1, 3, 5-triphenoxybenzene core and triarylamine terminals | |||
WANG Baolin,XU Taoshan,SHAO Xiangfeng | |||
Chemistry 16 November 2015 | |||
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Abstract:A series of star-shaped fluorescent molecules (2-5), employing 1,3,5-triphenoxybenzene as core and triarylamine as terminal groups, were synthesized through a facile three-step approach. The stability, solid state structure, and photophysical properties of 2-5 were investigated. In comparison with pristine triphenylamine, the present star-shaped compounds display the strong fluorescence with high fluorescence quantum yields up to 81.8 %. Besides, the influence of the aryls on the electronic properties of the resulting star-shaped molecules has been evaluated. | |||
TO cite this article:WANG Baolin,XU Taoshan,SHAO Xiangfeng. Synthesis and photophysical properties of star-shaped fluorescent molecules composed of 1, 3, 5-triphenoxybenzene core and triarylamine terminals[OL].[16 November 2015] http://en.paper.edu.cn/en_releasepaper/content/4661199 |
10. Efficient pyrido[1,2-a]benzimidazole formation from 2-aminopyridines and cyclohexanones under metal-free conditions | |||
Xie Yanjun,Chen Xiangui,Deng Guojun | |||
Chemistry 16 September 2015 | |||
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Abstract:An efficient procedure for pyrido[1,2-a]benzimidazole preparation from 2-aminopyridines and cyclohexanones under metal-free conditions is described. Iodine could smoothly mediate this kind of transformation without the aid of metal catalyst. Oxygen was used as an environmentally benign oxidant to give the corresponding products in good to high yields. The reaction showed good substrate scope and various functional groups such alkyl, ester, and halogens were well tolerated under the optimized reaction conditions. This method affords an efficient approach for biologically active nitrogen-containing heterocycles using non-aromatic cyclohexanones as the aryl source. | |||
TO cite this article:Xie Yanjun,Chen Xiangui,Deng Guojun. Efficient pyrido[1,2-a]benzimidazole formation from 2-aminopyridines and cyclohexanones under metal-free conditions[OL].[16 September 2015] http://en.paper.edu.cn/en_releasepaper/content/4655112 |
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