2128-93-0Relevant articles and documents
Self-Supported Ligands as a Platform for Catalysis: Use of a Polymeric Oxime in a Recyclable Palladacycle Precatalyst for Suzuki-Miyaura Reactions
Yang, Yun-Chin,Toy, Patrick H.
, p. 1319 - 1324 (2014)
A self-supported oxime palladacycle precatalyst for Suzuki Miyaura reactions was synthesized based on the polyether ether ketone architecture. This precatalyst was found to be highly efficient in Suzuki-Miyaura reactions when aryl bromides were used as substrates, but was less efficient in cross-coupling reactions when aryl chlorides were used. The polymeric palladacycle could be recovered and reused up to four times in such reactions, affording excellent yield of the desired product. The approach represents a novel strategy for generating such self-supported complexes for catalysis.Georg Thieme Verlag Stuttgart. New York.
Solution-dispersible, colloidal, conjugated porous polymer networks with entrapped palladium nanocrystals for heterogeneous catalysis of the Suzuki-Miyaura coupling reaction
Zhang, Peng,Weng, Zhihuan,Guo, Jia,Wang, Changchun
, p. 5243 - 5249 (2011)
Conjugated nanoporous polymer colloids (CNPCs) consisting of covalently cross-linked poly(p-phenyleneethynylene) networks were synthesized by using the Sonogashira coupling reaction in a toluene-in-water miniemulsion. The synthesized CNPCs having a uniform particle size distribution exhibit high porosity with a specific surface area of 421 m2/g and a dual distribution of pore size in the micropore and mesopore ranges. They are amenable to postfunctionalization and enhancement of their dispersibility in solvents, and retain their native photoluminescence. The modified CNPCs allow for in situ incorporation of palladium nanocrystals to form the Pd@CNPC composite materials. The Pd@CNPCs are validated to have excellent catalytic activity, outstanding reusability, and exceptionally high TOF (44100 h -1) for the Suzuki-Miyaura coupling reaction.
Modified zeolite immobilized palladium for ligand-free Suzuki-Miyaura cross-coupling reaction
Kumbhar, Arjun,Kamble, Santosh,Mane, Anand,Jha, Ratnesh,Salunkhe, Rajashri
, p. 29 - 34 (2013)
A palladium-based catalyst supported on modified ZSM-5 was successfully prepared by a facile procedure. The prepared heterogeneous catalyst Pd@desilicated ZSM-5 showed an excellent catalytic activity at very low Pd loading (0.02 mol%) for the ligand-free Suzuki-Miyaura coupling reactions of various aryl bromides affording excellent yields of the products. The prepared catalyst presents good recyclability, over four catalytic cycles.
Controlled Synthesis of Palladium Nanocubes as an Efficient Nanocatalyst for Suzuki-Miyaura Cross-Coupling and Reduction of p-Nitrophenol
Bhavya, M.,Bhol, Prangya,Kandathil, Vishal,Patil, Siddappa A.,Samal, Akshaya K.,Swain, Swarnalata
, p. 5208 - 5218 (2020)
Anisotropic nanocatalysts have attracted considerable attention in comparison to bulk/nanocatalysts for their enhanced activity and reactivity. The demand toward anisotropic palladium (Pd) nanostructures has increased rapidly in the field of catalysis. Pd is a well-known active catalyst for several carbon-carbon (C-C) cross-coupling reactions; among them, the Suzuki-Miyaura cross-coupling reaction is one of the most versatile and dominant methods for constructing the extraordinarily useful unsymmetrical biaryls and also for hydrogenation of organic contaminants like p-nitrophenol (p-NP). This paper provides a brief explanation about the controlled synthesis, characterization, and catalytic activity of well-defined palladium nanocubes (Pd NCs) prepared by a seed-mediated method. The synthesized monodispersed Pd NCs were characterized by spectroscopic and microscopic tools such as UV-visible, XRD, FESEM, HRTEM, and EDS analyses. Pd NCs proved as an efficient catalyst for Suzuki-Miyaura cross-coupling reactions and p-NP reduction. The catalyst shows enhanced activity, greater stability, and higher selectivity with remarkable recyclability up to 92% for five consecutive cycles. The catalytic performance of the synthesized Pd NCs was also studied in the reduction of the organic contaminant p-NP, which showed an excellent performance screening of 99% conversion in 6 min.
Pearson,Buehler
, p. 533,535 (1972)
Reusable magnetic Pd:XCoy nanoalloys confined in mesoporous carbons for green Suzuki-Miyaura reactions
Enneiymy, Mohamed,Le Drian, Claude,Matei Ghimbeu, Camélia,Becht, Jean-Michel
, p. 17176 - 17182 (2018)
We report herein PdxCoy nanoalloys confined in mesoporous carbons (Pdx-Coy@MC) prepared by an eco-friendly one-pot approach consisting in the co-assembly of readily available and non-toxic carbon precursors (phloroglucinol, glyoxal) with a porogen template (pluronic F-127) and metallic salts (H2PdCl4 and Co(NO3)2·6H2O) followed by thermal annealing. Three PdxCoy@MC materials with different alloy compositions were prepared (C1: x/y = 90/10; C2: x/y = 75/25; C3 and C4: x/y = 50/50). The nanoalloys were uniformly distributed in the carbon framework and the particle sizes depended on the alloy composition. These composites were then used for Suzuki-Miyaura reactions using either H2O or a 1:1 H2O/EtOH mixture as solvent. The Pd50Co50@MC catalyst C3 proved to be the most efficient catalyst (in terms of efficiency and magnetic recovery) affording the coupling products in good to excellent yields. After reaction, C3 was recovered quantitatively by simple magnetic separation and reused up to six times without loss of efficiency. The amount of palladium lost in the reaction mixture after magnetic separation was very low (ca. 0.1 % wt of the amount initially used).
Selective Activation of Unstrained C(O)-C Bond in Ketone Suzuki-Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy
Zhong, Jing,Zhou, Wuxin,Yan, Xufei,Xia, Ying,Xiang, Haifeng,Zhou, Xiangge
, p. 1372 - 1377 (2022/02/23)
A Rh(I)-catalyzed ketone Suzuki-Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C(O)-C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.
Identification and optimization of biphenyl derivatives as novel tubulin inhibitors targeting colchicine-binding site overcoming multidrug resistance
Cheng, Bao,Zhu, Guirong,Meng, Linghua,Wu, Guolin,Chen, Qin,Ma, Shengming
, (2021/11/22)
Microtubule targeting agents (MTAs) are among the most successful chemotherapeutic drugs, but their efficacy is often limited by the development of multidrug resistance (MDR). Therefore, the development of novel MTAs with the ability to overcome MDR is urgently needed. In this contribution, through modification of the unsymmetric biaryl compounds, we discovered a novel compound dxy-1-175 with potent anti-proliferative activity against cancer cells. Mechanistic study revealed that dxy-1-175 inhibited tubulin polymerization by interacting with the colchicine-binding site of tubulin, which caused cell cycle arrest at G2/M phase. Based on the predicted binding model of dxy-1-175 with tubulin, a series of new 4-benzoylbiphenyl analogues were designed and synthesized. Among them, the hydrochloride compound 12e with improved solubility and good stability in human liver microsome, exhibited the most potent anti-proliferative activity with IC50 value in the low nanomolar range, and markedly inhibited the growth of breast cancer 4T1 xenograft in vivo. Notably, 12e effectively overcame P-gp-mediated MDR and our preliminary data suggested that 12e may not be a substrate of P-glycoprotein (P-gp). Taken together, our study reveals a novel MTA 12e targeting the colchicine-binding site with potent anticancer activity and the ability to circumvent MDR.