- Copper anchored on phosphorus g-C3N4as a highly efficient photocatalyst for the synthesis ofN-arylpyridin-2-amines
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A heterogeneous photocatalyst based on copper modified phosphorus doped g-C3N4(Cu/P-CN) has been prepared and characterized. This recyclable catalyst exhibited high photocatalytic activity for the synthesis ofN-arylpyridin-2-amine derivatives by the reaction of 2-aminopyridine and aryl boronic acid at room temperature under the irradiation of blue light. Importantly, the range of substrates for this coupling reaction has been expanded to include aryl boronic acids with strong electron-withdrawing groups as viable raw materials. In addition, this heterogeneous catalyst can be used at least 6 times while maintaining its catalytic activity.
- Di, Jia-Qi,Zhang, Mo,Chen, Yu-Xuan,Wang, Jin-Xin,Geng, Shan-Shan,Tang, Jia-Qi,Zhang, Zhan-Hui
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p. 1041 - 1049
(2021/02/09)
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- Iridium(III)-Catalyzed Tandem Annulation of Pyridine-Substituted Anilines and α-Cl Ketones for Obtaining 2-Arylindoles
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A facile and expeditious protocol for the synthesis of 2-arylindole compounds from readily available N-(2-pyridyl)anilines and commercially available α-Cl ketones through iridium-catalyzed C-H activation and cyclization is reported here. As a complementary approach to the conventional strategies for indole synthesis, the transformation exhibits powerful reactivity, tolerates a large number of functional groups, and proceeds with good to excellent yields under mild conditions, providing a straightforward method to obtain structurally diverse and valuable indole scaffolds. Furthermore, the reaction could be easily scaled up to gram scale.
- Cui, Xin-Feng,Qiao, Xin,Wang, He-Song,Huang, Guo-Sheng
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p. 13517 - 13528
(2020/12/15)
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- Anticancer-Active N-Heteroaryl Amines Syntheses: Nucleophilic Amination of N-Heteroaryl Alkyl Ethers with Amines
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A mild amination protocol of N-heteroaryl alkyl ethers with various amines is described. This transformation is achieved by utilizing simple and readily available base as promoter via C-O bond cleavage, offering a new amination strategy to access several anticancer-active compounds. This work is highlighted by the excellent functional group compatibility, scalability, wide substrate scope, and easy derivatization of a variety of drugs.
- Wang, Xia,Yang, Qiu-Xia,Long, Cheng-Yu,Tan, Yan,Qu, Yi-Xin,Su, Min-Hui,Huang, Si-Jie,Tan, Weihong,Wang, Xue-Qiang
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supporting information
p. 5111 - 5115
(2019/07/03)
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- Ruthenium-catalyzed synthesis of indole derivatives from: N -aryl-2-aminopyridines and alpha-carbonyl sulfoxonium ylides
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Indole is a ubiquitous structural motif with important applications in many areas of chemistry. Given this, a simple and efficient Ru(ii)-catalyzed synthesis of indole via intermolecular annulation of N-aryl-2-aminopyridines and sulfoxonium ylides was proposed and accomplished. Excellent selectivity and good functional group tolerance of this transformation were observed. This protocol provides easy access to a wide variety of useful indoles in the presence of a commercially available [Ru(p-cymene)Cl2]2 catalyst. A possible mechanism for the reaction pathway was also proposed. More importantly, this reaction will offer a useful method for the construction of enantioenriched indole frameworks.
- Cui, Xin-Feng,Ban, Zi-Hui,Tian, Wa-Fa,Hu, Fang-Peng,Zhou, Xiao-Qiang,Ma, Hao-Jie,Zhan, Zhen-Zhen,Huang, Guo-Sheng
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supporting information
p. 240 - 243
(2019/01/10)
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- Synthesis method of aza-arylamine compound and aza-arylamine compound
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The invention provides a synthesis method of an aza-arylamine compound as shown in a formula (I). The synthesis method comprises the following steps: an aza aromatic hydrocarbon compound as shown in aformula (II) reacts with an amine compound as shown in a formula (III) in presence of alkali and under a heating condition, so that u X substituent groups on an A ring of the compound as shown in theformula (II) are substituted by NRR in the compound as shown in the formula (III), and the compound as shown in the formula (I) is obtained, wherein A is an aza six-membered aromatic ring or five-membered aromatic ring, and is an independent single ring or is fused with a ring B; X refers to that the A ring has at least n X substituent groups, each X substituent group is independently selected from the group consisting of F, Cl, Br, I, CN, alkoxy of C and alkylthio of C, and n is a positive integer selected from 1-5; and the alkali is one or a mixture of more selected fromof BuOK, BuONa, BuONa, KHMDS, NaHMDS and LiHMDS. The synthesis method provided by the invention does not need the use of transition metal catalysts, is simple and convenient to operate, is economical and practical and is environmentally friendly. In addition, the invention also provides the aza-arylamine compound prepared by the method.
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Paragraph 0059; 0060; 0061; 0086
(2019/04/26)
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- Synthesis of novel semi-squaraine derivatives and application in efficient dye-sensitized solar cells
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A series of novel semi-squaraine sensitizers with various architectures and anchors have been synthesized and utilized in dye-sensitized solar cells. These dyes combine indole- or carboline-based electron rich units with strongly electron-withdrawing cyanoacetate moieties or other functional anchoring moieties. They were thoroughly characterized as per their structural, optical and electrochemical properties and the behavior of the as-prepared solar cells were examined in detail using linear sweep voltammetry, electrochemical impedance spectroscopy and DFT calculations. Amongst the herein reported dyes, AKSq1, incorporating a free hydroxyl group directly attached to the squarate ring, exerts the optimum performance in dye-sensitized solar cells, despite the fact that this dye presents the lowest extinction coefficient among the molecules under study. AKSq1 demonstrates power conversion efficiency of 2.63%, about 14% higher than the efficiency obtained with the corresponding reference dye, the commercially available, high-performance, metal-free dye D35, under the same cell fabrication and measuring conditions. This result is attributed to the presence of free squaryl hydroxyl moiety ensuring efficient dye chemisorption and the existence of a lipophilic dodecyl group preventing the aggregation of the squaraine sensitizer onto the semiconductor's surface either by itself, or via increased intercalation of the C12 chain with the chenodeoxycholic acid coadsorbent.
- Kabanakis, Antonios N.,Bidikoudi, Maria,Elsenety, Mohamed M.,Vougioukalakis, Georgios C.,Falaras, Polycarpos
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p. 308 - 318
(2019/03/05)
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- Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling
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The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.
- Roscales, Silvia,Csák?, Aurelio G.
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supporting information
p. 1667 - 1671
(2018/03/23)
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- Ligand free copper-catalyzed N-arylation of heteroarylamines
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An efficient protocol for ligand-free Cu-catalyzed N-arylation of heteroarylamines has been developed. With the use of 1% CuI, a wide range of aryl iodides and bromides coupled with heteroarylamines to afford the corresponding products in high yields. Further, this protocol is particularly suitable for reactions of the most hindered aryl iodides with 2-aminopyridines.
- Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Liu, Yang,Ning, Shunhua
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supporting information
p. 7121 - 7123
(2015/01/08)
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- Palladium(II)-catalyzed direct ortho arylation of 4-methyl-N-phenylpyridin- 2-amines via C-H activation/C-C coupling and synthetic applications
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The direct ortho arylation of 4-methyl-N-phenylpyridin-2-amines via palladium(II)-catalyzed C-H activation is described. Treatment of 4-methyl-N-phenylpyridin-2-amine with potassium aryltrifluoroborate using 10 mol % of palladium(II) acetate as the catalyst, 2 equiv of copper(II) acetate as the oxidant, and 1 equiv of p-benzoquinone in tert-butyl alcohol gave ortho-arylated products in modest to excellent yields. This reaction shows good functional group compatibility. A series of 1H NMR titration experiments and controlled experiments elucidating the reaction mechanism were carried out. The key intermediate, 4-methyl-N-phenylpyridin-2-amine palladacycle, was isolated and characterized by X-ray crystallography. The advanced transformations of ortho-phenylated 4-methyl-N-phenylpyridin-2-amine to N-(4-methylpyridin-2-yl)-9H-carbazole, biphenyl-2-amine, and 3-methyl-6-phenylpyrido[1,2-a]benzimidazole were successfully demonstrated as potential synthetic applications.
- Chu, Jean-Ho,Huang, Hao-Ping,Hsu, Wen-Ting,Chen, Shih-Tien,Wu, Ming-Jung
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p. 1190 - 1204
(2014/04/03)
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- C-H cycloamination of N-aryl-2-aminopyridines and N-arylamidines catalyzed by an in situ generated hypervalent iodine(iii) reagent
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A metal-free synthesis of diversified pyrido[1,2-a]benzimidazoles and 1H-benzo[d]imidazoles from N-aryl-2-aminopyridines and N-arylamidines has been developed. The C-H cycloamination reaction was catalyzed by hypervalent iodine(iii) species generated in situ from iodobenzene (catalytic) and peracetic acid (stoichiometric). The reaction proceeded smoothly at ambient temperature to provide the corresponding N-heterocycles in good to excellent yields.
- He, Yimiao,Huang, Jinbo,Liang, Dongdong,Liu, Lanying,Zhu, Qiang
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supporting information
p. 7352 - 7354
(2013/09/23)
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- Palladium-catalyzed oxidative alkynylation of arene C-H bond using the chelation-assisted strategy
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Palladium-catalyzed alkynylation of arene C-H bonds with (triisopropylsilyl)acetylene was developed for the first time under oxidative conditions in the present study. Among various type of directing groups examined, the N-phenyl-2-aminopyridine skeleton was shown to be most effective and selective for the Pd-catalyzed direct alkynylation reaction, and the desired alkynylated products were obtained in moderate to good yields.
- Kim, Seok Hwan,Park, Sae Hume,Chang, Sukbok
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supporting information; experimental part
p. 5162 - 5166
(2012/07/31)
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- A direct intramolecular C-H amination reaction cocatalyzed by copper(II) and iron(III) as part of an efficient route for the synthesis of pyrido[1,2-a ]benzimidazoles from N-aryl-2-aminopyridines
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A novel and efficient synthesis of pyrido[1,2-a]benzimidazoles through direct intramolecular aromatic C-H amination of N-aryl-2-aminopyridines has been developed. The reaction, cocatalyzed by Cu(OAc)2 and Fe(NO 3)3?9H
- Wang, Honggen,Wang, Yong,Peng, Changlan,Zhang, Jiancun,Zhu, Qiang
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supporting information; experimental part
p. 13217 - 13219
(2010/11/04)
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- Identification of G protein-coupled receptor 120-selective agonists derived from PPARγ agonists
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A weak, nonselective G protein-coupled receptor 120 (GPR 120) agonist 10 was found by screening a series of carboxylic acids derived from the peroxisome proliferator-activated receptor γ (PPARγ) agonist 3. Modification based on the homology model of GPR12
- Suzuki, Takayoshi,Igari, Sou-Ichi,Hirasawa, Akira,Hata, Mie,Ishiguro, Masaji,Fujieda, Hiroki,Itoh, Yukihiro,Hirano, Tatsuya,Nakagawa, Hidehiko,Ogura, Michitaka,Makishima, Makoto,Tsujimoto, Gozoh,Miyata, Naoki
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supporting information; experimental part
p. 7640 - 7644
(2009/11/30)
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