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.
Synthesis and characterization of Pd-γ-Fe2O3 nanocomposite and its application as a magnetically recyclable catalyst in ligand-free Suzuki-Miyaura reaction in water
Paul, Dipankar,Rudra, Siddheswar,Rahman, Prabin,Khatua, Snehadrinarayan,Pradhan, Mukul,Chatterjee, Paresh Nath
, p. 96 - 102 (2018)
A novel redox-driven method to synthesize Pd-γ-Fe2O3 nanocomposite from Fe3O4 and PdCl2 under modified hydrothermal technique has been developed. The synthesized nanocomposite was characterized by XRD, FT-IR, XPS, FESEM, TEM and EDX to understand the composition as well as morphology. The Pd-γ-Fe2O3 nanocomposite was found to show excellent catalytic activity towards Suzuki-Miyaura cross-coupling reactions in water without the assistance of ligands, organic solvents or phase transfer catalysts. A wide range of functional substitutions in aryl halide as well as arylboronic acid moieties is tolerated in the developed protocol. The nanocatalyst can be recovered magnetically, and reused up to six cycles without significant loss in its catalytic activity.
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.
Carboxylic phosphoric anhydrides as a new coupling partner in Pd-catalyzed coupling reactions: A new ketone synthesis
Lim, Kyoung-Chan,Hong, Young-Taek,Kim, Sunggak
, p. 1851 - 1854 (2006)
The Pd-catalyzed cross-coupling reactions of carboxylic phosphoric anhydrides with organoboronic acids or organostannanes afforded the corresponding ketones. The intramolecular Heck reaction was successful with carboxylic phosphoric anhydrides as a coupling partner. Georg Thieme Verlag Stuttgart.
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.
Ultra-small palladium nano-particles synthesized using bulky S/Se and N donor ligands as a stabilizer: Application as catalysts for Suzuki-Miyaura coupling
Oswal, Preeti,Arora, Aayushi,Kaushal, Jolly,Rao, Gyandshwar Kumar,Kumar, Sushil,Singh, Ajai K.,Kumar, Arun
, p. 22313 - 22319 (2019)
Two chalcogenated ligands L1 and L2 containing anthracene core and amine functionality have been synthesized. Both the ligands have been characterized using 1H and 13C{1H} NMR techniques. The structure of L1 has also been corroborated by single crystal X-ray diffraction. Application of L1 and L2 as stabilizers for palladium nano-particles (NPs) has been explored and six different types of NPs 1-6 have been prepared by varying the quantity of stabilizer. The nano-particles have been characterized by PXRD, EDX, and HRTEM techniques. The size of NPs has been found to be in the range of ～1-2 nm, 2-3 nm, 4-6 nm, 1-2 nm, 1-2 nm and 3-5 nm for 1-6 respectively. The catalytic activities of 1-6 have been explored for Suzuki-Miyaura coupling of phenyl boronic acid with various aryl halides. These NPs showed good catalytic activity for various aryl chlorides/bromides at low catalyst loading (5 mg). Among 1-6, the highest activity has been observed for NPs 1, probably due to their relatively small size and high uniformity in the dispersion. The recyclability of the NPs upto 5 catalytic cycles is a distinct advantage.
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.
Direct synthesis of ferrocenylmethylphosphines from ferrocenylmethyl alcohols and their application as ligands for room temperature Pd(0)-catalyzed Suzuki cross-couplings of aryl bromides
Tang, Zhen-Yu,Lu, Yong,Hu, Qiao-Sheng
, p. 297 - 300 (2003)
(Matrix presented) The direct, high-yield conversion of readily available ferrocenylmethyl alcohols to ferrocenylmethylphosphines and the application of ferrocenylmethylphosphines as efficient ligands for room temperature Suzuki cross-coupling reaction of aryl bromides with phenylboronic acid are reported. The procedure of directly converting ferrocenylmethyl alcohols to ferrocenylmethylphosphines described here should find applications in the synthesis of many metallocenylmethylphosphines including optically active ones.
Catalytic reactivity of the complexes [Pd{(Ph2P)2N(tBu)-P,P′}X2], X = Cl, Br, I, in the Suzuki-Miyaura C?C coupling reaction: Probing effects of the halogeno ligand X? and the ligand's tBu group
Ioannou, Polydoros-Chrysovalantis,Arbez-Gindre, Cécile,Zoumpanioti, Maria,Raptopoulou, Catherine P.,Psycharis, Vassilis,Kostas, Ioannis D.,Kyritsis, Panayotis
, p. 40 - 46 (2019)
The synthesis, as well as the spectroscopic and structural characterization of three analogous palladium(II) complexes, [Pd{(Ph2P)2N(tBu)-κ2P,P′}X2], X = Cl, Br, I, is presented. X-ray crystallography studies revealed a similar square planar PdP2X2 first coordination sphere among the three complexes. The catalytic reactivity of these complexes was tested in the Suzuki-Miyaura coupling reaction, showing that the X = Cl, Br, complexes are more active than the X = I analogue. The differences in the catalytic reactivity within this series of complexes, as well as comparisons with similar palladium(II) catalysts reported in the literature, are discussed with respect to the different electronegativity of the three halogens and the strong +I inductive effect of the ligand's tBu group.
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).
