27331-34-6Relevant academic research and scientific papers
Hydrophilic CNC-pincer palladium complexes: A source for highly efficient, recyclable homogeneous catalysts in Suzuki-Miyaura cross-coupling
Churruca, Fatima,SanMartin, Raul,Ines, Blanca,Tellitu, Imanol,Dominguez, Esther
, p. 1836 - 1840 (2006)
The Suzuki biaryl coupling of a range of electronically dissimilar arylboronic acids and aryl bromides is performed in neat water with excellent to quantitative yields by means of a new CNC-pincer palladium catalyst that is soluble in water due to its para-carboxy group. Extremely high turn-over numbers and frequencies combined with a remarkable robustness allow an effective catalyst reuse in sustainable conditions.
Synthesis and characterization of palladium nanoparticles immobilized on graphene oxide functionalized with triethylenetetramine or 2,6-diaminopyridine and application for the Suzuki cross-coupling reaction
Mirza-Aghayan, Maryam,Mohammadi, Marzieh,Boukherroub, Rabah
, (2021/11/22)
Graphene oxide (GO) was functionalized with two organic ligands, triethylenetetramine (TETA) or 2,6-diaminopyridine (DAP), followed by palladium nanoparticles (Pd NPs) for the synthesis of Pd NPs/GO-TETA and Pd NPs/GO-DAP nanocomposites, respectively. The two heterogeneous nanocomposites were fully characterized and their efficiency was investigated for C[sbnd]C bond formation for the synthesis of biaryl compounds via the Suzuki cross-coupling reaction of aryl halides with arylboronic acid derivatives. The obtained results indicated that the Pd NPs/GO-TETA nanocomposite was more effective in the Suzuki coupling reaction as compared to Pd NPs/GO-DAP. Thus, the Suzuki cross-coupling reaction of different aryl halides with arylboronic acid derivatives using Pd NPs/GO-TETA nanocomposite catalyst in the presence of Na2CO3 as base in DMF/H2O (1/1) as solvent at 90 °C was carried out to afford the desired biaryl compounds in high to excellent yields (81–100%) and short reaction times (10–90 min). Additionally, Pd NPs/GO-TETA nanocomposite can be recovered and reused for 8 consecutive runs without any apparent loss of its catalytic activity, proving its high stability and potential use in organic transformations.
Suzuki-Miyaura Cross-Coupling Reaction with Potassium Aryltrifluoroborate in Pure Water Using Recyclable Nanoparticle Catalyst
Kawase, Misa,Matsuoka, Kyosuke,Shinagawa, Tsutomu,Hamasaka, Go,Uozumi, Yasuhiro,Shimomura, Osamu,Ohtaka, Atsushi
, p. 57 - 61 (2021/11/13)
This paper describes the Suzuki Miyaura cross-coupling reaction of aryl bromides with potassium aryltrifluoroborates in water catalyzed by linear polystyrene-stabilized PdO nanoparticles (PSPdONPs). The reaction of aryl bromides having electron-withdrawing groups or electron-donating groups took place smoothly to give the corresponding coupling product in high yields. The catalyst recycles five times without significant loss of catalytic activity although a little bit increase in size of PdNPs was observed after the reaction.
Highly Active Fe3O4@SBA-15@NHC-Pd Catalyst for Suzuki–Miyaura Cross-Coupling Reaction
?zdemir, ?smail,Akko?, Mitat,Alt?n, Serdar,Bu?day, Nesrin,Ya?ar, Sedat
, (2021/08/03)
A novel Pd-NHC functionalized magnetic Fe3O4@SBA-15@NHC-Pd was synthesized and used as an efficient heterogeneous catalyst in the Suzuki–Miyaura C–C bond formation reactions. The Fe3O4@SBA-15@NHC-Pd characterized by X-Ray Diffraction (XRD), X-ray Photoelectron Spectroscopy (XPS), Fourier Transform Infrared (FTIR) spectroscopy, Scanning Electron Microscopy (SEM), Transmission Electron Microscopy?(TEM), Energy Dispersive X-ray analysis (EDX), Thermogravimetric Analysis (TGA), Differential Thermal Analysis (DTA). The Inductively Coupled Plasma-Optical emission spectroscopy (ICP-OES)?analysis was used to determine the exact amount of Pd (0.33?wt%) in Fe3O4@SBA-15@NHC-Pd. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the catalyst's structure, while no reducing agent was used. The NHC moieties in the catalyst structure could be stabilize Pd(0) nanoparticles prevents agglomeration. The magnetic catalyst was effectively used in the Suzuki–Miyaura cross-coupling reaction of substituted phenylboronic acid derivatives with (hetero)aryl bromides in the presence of a K2CO3 at room temperature in aqueous media and magnetic catalyst could be simply extracted from the reaction mixture by an external magnet. Different aryl bromides were converted to coupled-products in excellent yields with spectacular TOFs values (up to 1,960,339?h?1); in the presence of 1?mg of Fe3O4@SBA-15@NHC-Pd catalyst (contains 3.1 × 10–6?mol% Pd) at room temperature in aqueous media. After reusability experiments, it is found that this catalyst was effectively used up to ten times in the reaction with almost consistent catalytic efficiency. A decrease in the activity of the 10th reused catalyst was found as 9%. Graphic Abstract: [Figure not available: see fulltext.]
Nickel/β-CD-catalyzed Suzuki–Miyaura cross-coupling of aryl boronic acids with aryl halides in water
Payamifar, Sara,Kazemi, Foad,Kaboudin, Babak
, (2021/07/16)
In this study, a convenient nickel-catalyzed protocol has been introduced for the Suzuki–Miyaura coupling reaction. A simple mixture of Ni(II) and unfunctionalized β-cyclodextrin (β-CD) was used to cross-coupling of aryl halides with aryl boronic acids for the synthesis of biaryls in water. β-CD is a water-soluble seminatural cyclic oligosaccharide, environmentally friendly biomaterial, inexpensive, and commercially available ligand. This ligand with low solubility in usual organic solvents has been used for the synthesis of biaryls in good to excellent yields. The cross-coupling results in the presence of Ni(II)/β-CD catalytic system showed that the coupling reaction carried out with appropriate yields for both electron-rich and electron-deficient aryl halides. The coupling reaction completed in water as a green solvent. The catalyst was also recycled for four runs with a small decrease in its catalytic activity. The presented new method allows an easier and more cost-efficient synthesis of biaryls from the reaction of arylboronic acids with various aryl halides in water.
C(sp2)-C(sp2) Suzuki cross-coupling of arylammonium salts catalyzed by a stable Pd–NHC complex
Tang, Huiling,Liu, Mengna,Zhu, Meiqi,Cui, Benqiang,Shi, Yanhui,Cao, Changsheng
, (2021/09/15)
We have developed the Suzuki-Miyaura cross-coupling of aryl ammonium salts via C–N bond activation catalyzed by an easily prepared and bench-stable palladium-N-heterocyclic carbene complex. The reaction proceeded well under mild conditions with phenylboronic acid, pinacol ester or anhydride and provided yields of products up to 97% with good functional group compatibility. The direct arylation of arylamine can be performed by a two-step one-pot process and the protocol can be performed on the gram scale.
MeOTf-catalyzed formal [4?+?2] annulations of styrene oxides with alkynes leading to polysubstituted naphthalenes through sequential electrophilic cyclization/ring expansion
Chen, Chao,Xi, Chanjuan,Zhang, Zeyu,Zou, Song
supporting information, (2021/12/30)
MeOTf-catalyzed formal [4 + 2] annulation of styrene oxides with alkynes to afford polysubstituted naphthalenes has been realized, which undergoes sequential electrophilic cyclization/ring expansion. A range of substrates were tolerated in the formation of naphthalene derivatives with high regioselectivity in satisfactory yields. The reaction could also be carried out on gram scale.
N-Aroylsulfonamide-Photofragmentation (ASAP)-A Versatile Route to Biaryls
Wessig, Pablo,Krebs, Saskia
, p. 6367 - 6374 (2021/09/29)
The photochemical fragmentation of N-aroylsulfonamides 9 (ASAP) is a powerful method for the preparation of various biaryls. Compounds 9 are easily accessible in two steps from amines by treatment with arenesulfonyl chlorides and aroyl chlorides. Many of these compounds were prepared for the first time. The irradiation takes place in a previously developed continuous-flow reactor using inexpensive UVB or UVC fluorescent lamps. Isocyanates and sulphur dioxide are formed as the only by-products. The ASAP tolerates a variety of functional groups and is even suited for the preparation of phenylnaphthalenes and terphenyls. The ASAP mechanism was elucidated by interaction of photophysical and quantum chemical (DFT) methods and revealed a spirocyclic biradical as key intermediate.
Precursors: Synthesis, Reactivity, and Catalytic Application to the Suzuki-Miyaura Reaction
D'Accriscio, Florian,Ohleier, Alexia,Nicolas, Emmanuel,Demange, Matthieu,Thillaye Du Boullay, Olivier,Saffon-Merceron, Nathalie,Fustier-Boutignon, Marie,Rezabal, Elixabete,Frison, Gilles,Nebra, Noel,Mézailles, Nicolas
supporting information, p. 1688 - 1699 (2020/06/04)
The complexes (Cy2PC3H6PCy2)Ni(η2-arene) (arene = toluene (3), naphthalene (4)) have been synthesized and studied in detail. Displacement reactions of the toluene ligand afford the complexes (Cy2PC3H6PCy2)Ni(η2-styrene) (5), (Cy2PC3H6PCy2)Ni(PhCN) (6), (Cy2PC3H6PCy2)Ni(CO)2 (7), (Cy2PC3H6PCy2)Ni(PPh3) (8), (Cy2PC3H6PCy2)Ni(PCy3) (9), {(Cy2PC3H6PCy2)Ni}2(μ-H)2 (10), (Cy2PC3H6PCy2)Ni(η2-CO2) (11), and [(Cy2PC3H6PCy2)Ni]2(μ,η2-1,5-COD) (12). The relative rates of ArCl oxidative addition at Ni complexes 3, 4, 6, 8, and 12 have been evaluated experimentally, and the mechanism has been calculated by DFT. Complexes 3 and 4 are efficient catalysts for the Suzuki-Miyaura reaction between chloroarenes and Ar′B(OH)2.
4-Amino-1,2,4-triazoles-3-thiones and 1,3,4-oxadiazoles-2-thiones·palladium(II) recoverable complexes as catalysts in the sustainable Suzuki-Miyaura cross-coupling reaction
Chehrouri, Manel,Moreno-Cabrerizo, Cristina,Othman, Adil A.,Chabour, Ihssene,Ferrándiz-Saperas, Marcos,Sempere, Inmaculada,D?nda?, H. Ali,de Gracia Retamosa,Sansano, José M.
, (2020/08/05)
The Suzuki-Miyaura cross-coupling reaction using 4-amino-1,2,4-triazoles and 1,3,4-oxadiazoles-2-thiones·palladium (II) is studied. The reaction is optimized and the most appropriate catalytic complex is tested with several aryl halides, boronic acids in an environmentally benign solvent system (H2O/EtOH). The recovery of the catalytic species is also surveyed because of the nature of the employed solvent. A domino process is efficiently carried out following the standard conditions. Several surface parameters of the ligands are analyzed and the resulting values are extrapolated to the insoluble palladium catalyst.
