10540-31-5Relevant articles and documents
Cost-effective bio-derived mesoporous carbon nanoparticles-supported palladium catalyst for nitroarene reduction and Suzuki–Miyaura coupling by microwave approach
Supriya,Ananthnag, Guddekoppa S.,Shetti, Vijayendra S.,Nagaraja,Hegde, Gurumurthy
, (2020)
A new heterogeneous catalyst was synthesized by immobilizing Pd on areca nut kernel-derived carbon nanospheres (CNSs). The CNSs, without any further activation processes, accommodated 3% of Pd on their surface. The new Pd/CNS material was used for the reduction of nitroarenes and Suzuki–Miyaura coupling of bromoarenes with aryl boronic acids. The reactions were conducted under microwave irradiation at 160 °C using 12 mol% of Pd/CNS (0.36% actual Pd content). The reduction of nitroarenes into their respective amino compounds was achieved in 10–20 min (conversion up to 100%); by contrast, the Suzuki–Miyaura reactions yielded up to 98% at 150 °C with 10 mol% of Pd/CNS catalyst. The products were identified using gas chromatography and nuclear magnetic resonance spectroscopy. The catalyst was isolated from reaction mixture and reused without any significant loss in the activity. Thus, the present work introduces one-pot-derived porous CNSs as efficient catalytic support to Pd, establishing an alternative to existing Pd/C in terms of cost and efficiency.
Palladium-catalyzed, ligand-free Suzuki reaction in water using aryl fluorosulfates
Liang, Qiaobin,Xing, Ping,Huang, Zuogang,Dong, Jiajia,Sharpless, K. Barry,Li, Xiaoxian,Jiang, Biao
, p. 1942 - 1945 (2015)
Aryl fluorosulfates were prepared by a simple method and employed as coupling partners in the Suzuki-Miyaura reaction. The cross-coupling reactions were performed in water under air at room temperature without ligands or additives such as surfactants or phase-transfer reagents and proceeded smoothly to give excellent yields. Aryl fluorosulfates could also be used as alternatives to halides or triflates in other coupling reactions.
Suzuki–Miyaura Coupling of (Hetero)Aryl Sulfones: Complementary Reactivity Enables Iterative Polyaryl Synthesis
Chatelain, Paul,Sau, Abhijit,Rowley, Christopher N.,Moran, Joseph
, p. 14959 - 14963 (2019)
Ideal organic syntheses involve the rapid construction of C?C bonds, with minimal use of functional group interconversions. The Suzuki–Miyaura cross-coupling (SMC) is a powerful way to form biaryl linkages, but the relatively similar reactivity of electrophilic partners makes iterative syntheses involving more than two sequential coupling events difficult to achieve without additional manipulations. Here we introduce (hetero)aryl sulfones as electrophilic coupling partners for the SMC reaction, which display an intermediate reactivity between those of typical aryl (pseudo)halides and nitroarenes. The new complementary reactivity allows for rapid sequential cross-coupling of arenes bearing chloride, sulfone and nitro leaving groups, affording non-symmetric ter- and quateraryls in only 2 or 3 steps, respectively. The SMC reactivity of (hetero)aryl sulfones is demonstrated in over 30 examples. Mechanistic experiments and DFT calculations are consistent with oxidative addition into the sulfone C?S bond as the turnover-limiting step. The further development of electrophilic cross-coupling partners with complementary reactivity may open new possibilities for divergent iterative synthesis starting from small pools of polyfunctionalized arenes.
Pd-nanoparticles catalyzed denitrogenative coupling of aryl halides with arylhydrazines: Greener approach for biaryls synthesis under ligand-free condition
Hegde, Rajeev V.,Ghosh, Arnab,Patil, Siddappa A.,Dateer, Ramesh B.
, (2019)
The greener approach for the synthesis of biaryl using palladium nanoparticle (Pd–NPs) catalyzed denitrogenative coupling between aryl hydrazine and aryl halides under ligand-free condition has been described. The phytochemicals of the black pepper extract plays a dual role in reduction of PdII to Pd0 and acts as stabilizing agent for Pd–NPs. The electronically diver's arylhydrazines and commercially available aryl halides are used for the synthesis of symmetrical and unsymmetrical biaryls in good to excellent yield. The mechanism is well supported by control experiment and the recyclability, turnover number and turnover frequency of biogenically synthesized Pd–NPs is studied.
Microwave enhanced ligand- and base-free cross-coupling of potassium aryltrifluoroborates salts with aryl triflates
Kabalka, George W.,Zhou, Li-Li,Naravane, Abhijit
, p. 6887 - 6889 (2006)
A microwave enhanced ligand- and base-free protocol for the cross-coupling of potassium aryltrifluoroborate salts with triflates is reported.
A simple and mild Suzuki reaction protocol using triethylamine as base and solvent
Li, Xinmin,Zhang, Hang,Hu, Qinghong,Jiang, Bo,Zeli, Yuan
, p. 3123 - 3132 (2018)
A simple and mild protocol for the palladium-catalyzed Suzuki reaction of aryl bromides and arylboronic acids is developed. The cross-coupling reactions can be performed at room temperature using 5.0 equiv. of Et3N as solvent and base without any ligands, and affording biaryl products in good yields. In addition, the chemoselecitive Suzuki reaction of bromo-N-methyliminodiacetic acid (MIDA) boronates with arylboronic acids can be achieved in this system, and various unsymmetrical terphenyls have been prepared in moderate yields by one-pot double Suzuki reactions.
Palladium nanoparticle supported on nitrogen-doped porous carbon: Investigation of structural properties and catalytic activity on Suzuki–Miyaura reactions
Bu?day, Nesrin,Alt?n, Serdar,Ya?ar, Sedat
, (2021)
Novel palladium-doped nanoporous carbon composite material obtained via thermolysis of amorphous zeolitic imidazolate framework (aZIF) was synthesized and used as an efficient catalyst on Suzuki–Miyaura cross-coupling reactions of aryl bromides. With this developed catalytic system, the Suzuki–Miyaura cross-coupling reaction was accomplished in aqueous solutions, and biaryls were obtained in good to excellent yields in a short reaction time. The APC-750@Pd catalyst was characterized by Fourier Transform Infrared spectroscopy (FTIR), X-ray Diffraction (XRD), Scanning Electron Eicroscopy (SEM), X-ray Photoelectron Spectroscopy (XPS), Transmission Electron Microscopy (TEM), Thermal Gravimetric Analysis (TGA), Differential Thermal Analysis (DTA), Inductively Coupled Plasma Mass Spectrometry (ICP-MS) and Brunauer–Emmett–Teller (BET) analysis tecniques. N-doped porous carbon material (NPC-1000) was synthesized by thermolysis from aZIF. Activated porous carbon material (APC-750) was fabricated via fused at 750°C with KOH from NPC-1000. The APC-750@Pd was obtained as a result of the interaction of APC-750 and PdCl2 in deionized water. The cross-coupling reaction of different aryl bromides with phenylboronic acid was investigated to show the potential of the APC-750@Pd in the Suzuki–Miyaura cross-coupling reactions. The APC-750@Pd catalyst could be recycled at least five times with a 15% loss of catalytic efficiency in this catalytic system.
Palladium-catalyzed Suzuki-Miyaura cross-couplings of aryl tosylates with potassium aryltrifluoroborates
Zhang, Liang,Meng, Tianhao,Wu, Jie
, p. 9346 - 9349 (2007)
(Chemical Equation Presented) Pd-catalyzed Suzuki-Miyaura cross-coupling reaction of aryl tosylates with potassium aryl trifluoroborate in the presence of bulky and electron-rich phosphine ligand is described. In addition, a useful chemoselective coupling of an aryl chloride in the presence of a tosyloxy group was demonstrated.
Highly Active Bimetallic Nickel-Palladium Alloy Nanoparticle Catalyzed Suzuki-Miyaura Reactions
Rai, Rohit Kumar,Gupta, Kavita,Behrens, Silke,Li, Jun,Xu, Qiang,Singh, Sanjay Kumar
, p. 1806 - 1812 (2015)
A bimetallic Ni-Pd alloy nanoparticle catalyst with a low palladium content (Ni0.90Pd0.10 nanocatalyst) was prepared and its catalytic performance in Suzuki-Miyaura reactions was evaluated along with that of other Ni-Pd nanocatalysts (with varying Ni/Pd molar ratios in the range of ≈0.25-0.75) and the corresponding monometallic, Ni and Pd, analogues. Notably, the bimetallic Ni0.90Pd0.10 alloy nanocatalyst performed exceptionally well for the synthesis of biaryls by employing a wide range of substituted aryl halides and arylboronic acids having electron-donating and electron-withdrawing groups, and they exhibited high recyclability in water/ethanol solution at moderate reaction temperatures. Catalyst poisoning tests and leaching experiments inferred the heterogeneous nature of the Ni0.90Pd0.10 nanocatalysts. The significant synergistic interactions between Ni and Pd account for the observed high catalytic efficacy of the Ni0.90Pd0.10 nanocatalyst. Up, up, and alloy! Highly active bimetallic Ni-Pd alloy nanocatalysts with high Ni/Pd molar ratios facilitate the Suzuki-Miyaura reactions of a wide range of aryl iodides/bromides and arylboronic acids to biaryls in high yields at moderate temperatures in water/ethanol solution. High synergistic interaction between Ni and Pd accounts for the observed high activity and recyclability of the bimetallic Ni-Pd nanocatalysts. FG=functional group.
Photocatalyzed Transition-Metal-Free Oxidative Cross-Coupling Reactions of Tetraorganoborates**
Music, Arif,Baumann, Andreas N.,Boser, Florian,Müller, Nicolas,Matz, Florian,Jagau, Thomas C.,Didier, Dorian
supporting information, p. 4322 - 4326 (2021/02/11)
Readily accessible tetraorganoborate salts undergo selective coupling reactions under blue light irradiation in the presence of catalytic amounts of transition-metal-free acridinium photocatalysts to furnish unsymmetrical biaryls, heterobiaryls and arylated olefins. This represents an interesting conceptual approach to forge C?C bonds between aryl, heteroaryl and alkenyl groups under smooth photochemical conditions. Computational studies were conducted to investigate the mechanism of the transformation.