2051-61-8Relevant articles and documents
Factorial design evaluation of the Suzuki cross-coupling reaction using a magnetically recoverable palladium catalyst
Guerra, Raíza R.G.,Martins, Felipe C.P.,Lima, Carolina G.S.,Gon?alves, Ricardo H.,Leite, Edson R.,Pereira-Filho, Edenir R.,Schwab, Ricardo S.
, p. 903 - 908 (2017)
A magnetically recoverable catalyst [Fe3O4@SiO2-AEAPTMS-Pd(II)] was prepared, fully characterized and had its catalytic activity evaluated on the Suzuki cross-coupling reaction under microwave irradiation. The reaction conditions for the synthesis of biaryl compounds was optimized in two stages - an initial fractional design 24, in which the parameters reaction time, temperature, solvent and catalyst loading were evaluated, followed by a Doehlert design. The factorial design proved to be a viable approach for obtaining the optimal reaction conditions based on a relatively small number of experiments. Additionally, the biaryl derivatives synthesized by this method were obtained with good to excellent yields (71–96%) and the recovery and reuse of the palladium catalyst was also evaluated.
Inorganic–organic hybrid nano magnetic based nickel complex as a novel, efficient and reusable nanocomposite for the synthesis of biphenyl compounds in green condition
Naeimi, Hossein,Kiani, Fatemeh
, p. 163 - 169 (2019)
The carbon–carbon cross coupling reactions through transition-metal-catalyzed processes has been significantly developed for their important synthetic applications. A novel and fantastic nickel-based catalyst supported on bis (propyl malononitrile) (NiFe2O4@SiO2-BPMN-Ni) was easily prepared and evaluated as heterogeneous nanocatalyst in Suzuki cross coupling reaction of various aryl halides and phenylboronic acid. The catalyst prepared and characterized by using fourier transform infrared (FT-IR), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), thermo gravimetric analysis (TGA) and vibrating sample magnetometer (VSM) techniques. Compare to the previous works, this procedure have advantages such as easy workup, high yields of products, environmentally benign and short reaction times. The catalyst can be separated by external magnet and reused six times without any significant loss of activity which is an additional sustainable characteristic of this method. The products have been confirmed by spectroscopic and physical data such as; IR, 1H NMR, and melting point.
Ultrasound-assisted synthesis of unsymmetrical biaryls by Stille cross-coupling reactions
Domini, Claudia E.,Silbestri, Gustavo F.,Fernández Band, Beatriz,Chopa, Alicia B.
, p. 410 - 414 (2012)
We describe herein an efficient method for the synthesis of unsymmetrically-substituted biphenyls using a sonochemical variation of the Stille coupling, whose results have also been compared with the conventional silent reaction. Ultrasound significantly enhances this useful organometallic transformation affording products in higher yields and in shorter reaction times than non-irradiated reactions. The scope has been explored with a selection of arylstannanes as precursors and, remarkably, no by-products resulting from homo-coupling could be detected.
A comparative Suzuki reaction of aryl halides using a new dimeric orthopalladated complex under conventional and microwave irradiation conditions
Hajipour, Abdol R.,Karami, Kazem,Tavakoli, Ghazal
, p. 401 - 405 (2012)
The cross-coupling reaction between phenylboronic acid and various types of aryl halides (Suzuki reaction) was carried out using a catalytic amount of a new phosphine-based catalyst under microwave irradiation. The reaction conditions were optimized and results showed that, by application of this catalytic system, N-methyl-2-pyrrolidone as the solvent and potassium carbonate as the base, reactions could be completed in a short reaction time with high to excellent yields. Copyright 2012 John Wiley & Sons, Ltd. The Suzuki reaction of aryl halides was carried out using a new catalyst under the optimized conditions. Application of microwave irradiation lead to very good results in a short time. Copyright
Palladium-catalyzed benzene arylation: Incorporation of catalytic pivalic acid as a proton shuttle and a key element in catalyst design
Lafrance, Marc,Fagnou, Keith
, p. 16496 - 16497 (2006)
A palladium-pivalic acid cocatalyst system has been developed that exhibits unprecedented reactivity in direct arylation. This reactivity is illustrated with the first examples of high yielding direct metalation-arylation reactions of a completely unactivated arene, benzene. Experimental and computational evidence indicates that the pivalate anion is a key component in the palladation/C-H bond breaking event, that it lowers the energy of C-H bond cleavage and acts as a catalytic proton shuttle from benzene to the stoichiometric carbonate base. Eight examples of substituted aryl bromides are included which undergo direct arylation with benzene in 55-85% yield Copyright
Cubical Palladium Nanoparticles on C@Fe3O4 for Nitro reduction, Suzuki-Miyaura Coupling and Sequential Reactions
Kumar, Basuvaraj Suresh,Amali, Arlin Jose,Pitchumani, Kasi
, p. 511 - 519 (2016)
Cubical Pd nanoparticles incorporated magnetically recyclable nanoreactor (Pd cNPs/C@Fe3O4) are found to be efficient catalysts for the hydrogenation or aromatic nitrocompounds, Suzuki-Miyaura coupling and the sequential reaction of [Formula presented] coupling followed by reduction of nitrobiphenyl substrates. A variety of aryl iodides, bromides and chlorides were coupled with phenylboronic acids to form corresponding biaryl products and variety of nitro aromatic compounds was hydrogenated with excellent yield and high TON. The catalytic activity of palladium cubical nanoparticles (Pd cNPs) embedded with excess of {100} surface facets are superior compared to Pd spherical nanoparticles (Pd sNPs) embedded with mixed surface facets. The catalytic efficiency remains unaltered even after five repeated cycles. The observed enhanced catalytic activity is attributed to the high density of low-coordinated Pd {100} atoms present at the surface of the Pd cNPs/C@Fe3O4 catalyst, confirmed by HR-TEM studies. Also, the catalyst is truly heterogeneous, highly stable, does not require any toxic ligands, has wide substrate scope in both nitroreduction and Suzuki-Miyaura coupling reaction along with the ability to catalyse in a sequential manner, magnetically separable from the reaction mixture and can be reused.
Ultrasonic accelerated coupling reaction using magnetically recyclable bis (propyl molononitril) Ni complex nanocatalyst: A novel, green and efficient synthesis of biphenyl derivatives
Kiani, Fatemeh,Naeimi, Hossein
, p. 267 - 274 (2018)
A novel, green and rapid sonochemical research to preparation of the biphenyls was carried out through the coupling reaction between various aryl halides and phenylboronic acid by using bis(propyl malononitrile) Ni (0) complex (NiFe2O4@SiO2-BPMN-Ni) as an efficient nano catalyst. The catalyst can be recycled via an external magnet and reused several times without considerable loss of its catalytic activity. Compare to the previous works, this procedure has advantages such as easy workup, high yields of products, environmentally benign and short reaction times. The novel nickel catalyst prepared and characterized by FT-IR, XRD, SEM, EDX, TGA and VSM techniques.
Suzuki cross-coupling reaction catalyzed by palladium-supported sepiolite
Shimizu, Ken-Ichi,Kan-No, Toshiki,Kodama, Tatsuya,Hagiwara, Hisahiro,Kitayama, Yoshie
, p. 5653 - 5655 (2002)
Palladium-supported sepiolite clay has effectively catalyzed the Suzuki cross-coupling reaction of phenylboronic acid with aryl halide including less reactive electron-rich aryl bromides.
Alumina as Solid-State Ligand in Enhancing the Redox Catalytic Property of Iron Oxide Grafted AlSBA-15 towards Arylation of Arene
Rajendran, Chandran,Thirumoorthy, Kulandaivellu,Satishkumar, Govindaswamy,Landau, Miron V.
, p. 4768 - 4776 (2018)
2–8 wt % iron has been grafted over SBA-15 and 10 wt % alumina grafted SBA-15 (AlSBA-15) through selective extraction deposition technique using LaFeO3 as iron precursor in acidic solution. DRS-UV spectra confirmed the presence of iron as isolated Fe(III), Fe(III)-clusters and amorphous FeOx oligomers. SEM-EDX mapping, FT-IR, XPS, HR-TEM and 27Al MAS NMR characterisation results confirmed that iron grafted over AlSBA-15 preferentially reside on the alumina. The donor-acceptor interaction of grafted iron ions with alumina atoms displaying Lewis acid properties stabilized iron at higher oxidation state Fe(III+δ). This increased the BE of Fe2p electrons (XPS) and shifted the temperature of iron reduction in 2–8 wt %Fe/AlSBA-15 materials to higher value (600 °C) compared with Fe/SBA-15 (H2-TPR). In arylation of benzene, 8 wt %Fe/AlSBA-15 demonstrated excellent redox catalytic activity with TOF close to homogeneous catalyst and 82 % biphenyl yield. The catalyst demonstrated consistent catalytic performance for 7 cycles.
Direct arylation catalysis with chloro[8-(dimesitylboryl)quinoline-κN]copper(I)
Tamang, Sem Raj,Hoefelmeyer, James D.
, p. 2757 - 2762 (2016)
We report direct arylation of arylhalides with unactivated sp2 C-H bonds in benzene and naphthalene using a copper(I) catalyst featuring an ambiphilic ligand, (quinolin-8-yl)dimesitylborane. Direct arylation could be achieved with 0.2 mol % catalyst and 3 equivalents of base (KO(t-Bu)) at 80 °C to afford TON ≈160-190 over 40 hours.
