- A highly efficient and recyclable Pd(II) metallogel catalyst: A new scaffold for Suzuki-Miyaura coupling
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A convenient and practical procedure to prepare Pd(II) metallogel as a highly efficient and recyclable catalyst for Suzuki-Miyaura coupling has been developed. Such metallogel shows highly processable and reversible responses to thermal and mechanical stimuli. The xerogel is a highly efficient (0.005?mol% Pd) heterogeneous catalyst for Suzuki-Miyaura couplings with arylhalides and phenylboronic acids in excellent yield in water or ethanol under ambient atmosphere. The reaction could be scaled up to 10?gram scale with 0.001?mol% Pd catalyst loading with 99% yield. The catalyst can be recycled and reused at least seven times without loss of activity.
- Ye, Yu-Xin,Liu, Wan-Long,Ye, Bao-Hui
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- A new blue light-emitting terphenyl-bridged bisbenzimidazolium salts: Synthesis, crystal structure, and photophysical properties
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Eight novel terphenyl-bridged bisbenzimidazolium salts bearing N-alkyl side chains were synthesized by alkylation and quaternization of terphenyl-bridged bisbenzimidazoles with excess alkyl bromides, using sodium carbonate as the base in N,N-dimethylformamide solution. The bisbenzimidazolium salts showed good solubility in water and common organic solvents, such as dichloromethane, chloroform, methanol, acetonitrile, and N,N-dimethylformamide. They emitted violet-blue light (λmaxEm≈397-400nm) with fluorescence quantum yields of 0.65-0.78 in aqueous solution, whereas they emitted blue light (λmaxEm≈420-441nm) in thin films. The photoluminescent properties and crystal structure of the bisbenzimidazolium salts have been investigated.
- Luo, Zhonghua,Shi, Hong,Zhu, Hongjun,Song, Guangliang,Liu, Yuanyuan
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- Synthesis, characterization and catalytic performance of palladium supported on pyridine-based covalent organic polymer for Suzuki-Miyaura reaction
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A bipyridine-based covalent organic polymer (COP) was successfully synthesized by condensation of trimesoyl chloride (TMC) and 2,2′-bipyridine-5,5′-diamine (Bpy) under ambient conditions. This material was modified by coordination of PdCl2 to COP framework, affording a hybrid material, Pd@TMC-Bpy COP, which was applied as a highly efficient heterogeneous catalyst for Suzuki-Miyaura reaction under ligand-free conditions in ethyl lactate. The catalyst could be reused for five times without obvious loss of its activity.
- Han, Yi,Di, Jia-Qi,Zhao, Ai-Dong,Zhang, Zhan-Hui
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- Ligand-Free Bioinspired Suzuki–Miyaura Coupling Reactions using Aryltrifluoroborates as Effective Partners in Deep Eutectic Solvents
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Pd-catalyzed Suzuki–Miyaura cross-coupling between (hetero)aryl halides (Cl, Br, I) and versatile, moisture-stable mono- and bifunctional potassium aryltrifluoroborates proceeded efficiently and chemoselectively in air and under generally mild conditions; a catalyst loading as low as 1 mol % combined with Na2CO3 as a base in choline chloride/glycerol (1:2) deep eutectic solvent (DES) was used as a sustainable and environmentally responsible medium. The catalyst, base, and DES were easily and successfully recycled up to six times with an E-factor as low as 8.74. Valuable biaryls and terphenyl derivatives were furnished in yields of up to 98 %; over 50 reactions were compared and discussed. The methodology was applied for the synthesis of the nonsteroidal anti-inflammatory drugs Felbinac and Diflunisal.
- Dilauro, Giuseppe,García, Sergio Mata,Tagarelli, Donato,Vitale, Paola,Perna, Filippo M.,Capriati, Vito
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p. 3495 - 3501
(2018/09/21)
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- Catalytic synthesis of Bi- and teraryls in aqueous medium with palladium(II) complexes of 2-(pyridine-2-ylmethylsulfanyl)benzoic acid
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Suzuki-Miyaura coupling reactions of phenylboronic and 1,4-phenylenediboronic acid with ArBr to form bi- and teraryls have been efficiently catalyzed by the air- and moisture-insensitive complexes [PdCl2L1] [1, L1 = 2-(pyridine-2-ylmethyl)sulfanylbenzoic acid; 0.05-0.5 mol-%] and [Pd(L2-H)2] (2, L2-H = 2-pyridin-2-yl-benzo[b]thiophen-3-ol; 0.01-0.5 mol-%). The complexes were formed by the reaction of [Pd(CH3CN)2Cl2] with L1, and the catalysis proceeds in water for 1. The loading of 0.1-0.5 mol-% of Pd is very promising for the coupling reactions to form teraryls. The COOH group imparts solubility to 1 in water. Ligand L2 is formed by the unprecedented cyclization of L1 in the course of the complexation reaction. The yield of 2 increases with the reaction time (5 h: 70%; 24 h: 85%). The two complexes and L1 have been characterized by NMR spectroscopy (1H and 13C{1H}). The single-crystal structures of 1 and 2 have been solved, and the Pd-S, Pd-N, and Pd-O bond lengths are 2.269(2), 1.999(6)-2.057(2), and 1.9787(17) A?, respectively. Nanoparticles (NPs) with a narrow size distribution (ca. 3.0-5.5 nm for 80-85% of the particles) formed at the start of these reactions and appear to be important for the catalytic coupling. Poisoning experiments and a two-phase test have shown that the catalysis is largely homogeneous and involves [Pd0-PdII] processes. The bond lengths and angles calculated by DFT are consistent with the experimental ones.
- Prakash, Om,Joshi, Hemant,Sharma, Kamal Nayan,Sharma, Alpesh Kumar,Singh, Ajai K.
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p. 520 - 526
(2015/02/05)
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- Palladium nanoparticles catalyzed Suzuki cross-coupling reactions in ambient conditions
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An efficient pathway to synthesize biaryls and terphenyls through ligand-free palladium nanoparticles (PdNPs) catalyzed Suzuki cross-coupling reactions has been developed. Mild reaction conditions, high yields of desired products, absence of inert atmosphere and short reaction times are the notable features of this method.
- Mandali, Pavan Kumar,Chand, Dillip Kumar
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- Synthesis and photophysical properties of a series of thermally stable terphenyl-bridged bisbenzimidazoles
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Nine novel terphenyl-bridged bisbenzimidazoles were synthesized in high yield by the condensation of o-phenylenediamines and terphenyl dinitriles in the presence of polyphosphoric acid. The bisbenzimidazoles are thermally robust with high decomposition te
- Luo, Zhonghua,Zhu, Hongjun,Song, Guangliang,Chang, Jin,Liu, Rui
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p. 274 - 279
(2011/06/11)
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- Azaterphenyl diamidines as antileishmanial agents
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Eighteen diamidino azaterphenyls and analogues were evaluated as anti-leishmanials; nine of the compounds gave IC50 values less than 1 μM, five exhibited values less than 0.40 μM, and two gave values less than 0.10 μM in a Leishmania donovani a
- Hu, Laixing,Arafa, Reem K.,Ismail, Mohamed A.,Wenzler, Tanja,Brun, Reto,Munde, Manoj,Wilson, W. David,Nzimiro, Sandra,Samyesudhas, Serene,Werbovetz, Karl A.,Boykin, David W.
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p. 247 - 251
(2008/09/18)
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- Linear dicationic terphenyls and their aza analogues as antiparasitic agents
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Novel dicationic terphenyl compounds and their aza analogues. Methods for combating microbial infections with novel dicationic terphenyl compounds and their aza analogues. Processes for synthesizing novel dicationic terphenyl compounds and their aza analo
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Page/Page column 37-38
(2010/11/25)
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- Synthesis, DNA affinity, and antiprotozoal activity of linear dications: Terphenyl diamidines and analogues
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Diamidines 10a-g and 18a,b were obtained from dinitriles 9a-g and 15a,b by treatment with lithium trimethylsilylamide or upon hydrogenation of bis-O-acetoxyamidoximes. Dinitriles 9a-g were prepared via Suzuki reactions between arylboronic acids and arylni
- Ismail, Mohamed A.,Arafa, Reem K.,Brun, Reto,Wenzler, Tanja,Miao, Yi,Wilson, W. David,Generaux, Claudia,Bridges, Arlene,Hall, James E.,Boykin, David W.
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p. 5324 - 5332
(2007/10/03)
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