58244-47-6Relevant academic research and scientific papers
Ligation state of nickel during C–O bond activation with monodentate phosphines
Hooker, Leidy V.,Neufeldt, Sharon R.
, p. 6717 - 6725 (2018)
The oxidative addition of phenolic electrophiles at Ni(0) in the presence of monodentate phosphine ligands was studied with both dispersion-free and dispersion-containing DFT methods. With the popular bulky ligand PCy3, consideration of dispersion has a striking effect on the predicted ligation state of nickel during oxidative addition of aryl sulfamates. Dispersion-containing methods such as M06L indicate a clear preference for a bis-phosphine ligated transition state (TS), while dispersion free methods like B3LYP strongly favor a mono-phosphine ligated TS. This discrepancy in predicted ligation state is also found with small phosphines (PMe3) in combination with some aryl electrophiles (carbamates, acetates, pivalates, chlorides), but a bis-PMe3-ligated TS is predicted regardless of dispersion for other electrophiles (sulfamates, mesylates, tosylates). DFT calculations that include dispersion also offer a possible explanation for the observed poor efficacy of PtBu3 as a ligand in Ni-catalyzed cross-coupling reactions.
Preparation and characterization of a Cu complex based on 2,2′-bipyrimidine as a recyclable metal-organic framework for Suzuki coupling
Liu, Hongmei,Liu, Ming,Kiasadegh, Mehdi
, p. 2873 - 2885 (2021/12/31)
A Cu complex based on 2,2′-bipyrimidine ([CuBpm·2H2O]n) as a recyclable metal-organic framework (MOF) was used for the synthesis of biaryl derivatives by the Suzuki coupling reaction. The Suzuki reaction was performed with mixing of aryl halides with arylboronic acids in DMSO. The prepared catalyst was characterized by FT-IR, XRD, SEM, EDX, BET, BJH and ICP-AES analysis. [CuBpm·2H2O]n as catalyst demonstrated good to excellent yields for Suzuki reaction in comparison with other catalysts. The catalyst was recovered by a simple filtration and retained its activity even after several cycles.
An efficient clean and sustainable methodology for catalytic C-C coupling process over a Pd-free magnetically recoverable cobalt catalyst
Masteri-Farahani, Majid,Niakan, Mahsa
, (2022/03/27)
The Suzuki and Sonogashira coupling reactions are important processes in organic synthesis. However, to date, these reactions have been extensively examined using Pd-based catalysts in toxic organic solvents. Therefore, developing clean and inexpensive methodologies for these reactions remained a major challenge. Herein, by taking the advantages of thiol-ene click reaction, an easy and robust strategy for surface modification of magnetic graphene oxide with a dendrimer structure was successfully developed. Dendrimer-functionalized magnetic graphene oxide was then applied for the immobilization of Co nanoparticles. Transmission electron microscopy exhibited a homogeneous distribution of Co nanoparticles with the size of about 3 nm. The resultant nanocomposite revealed high efficiency in catalytic Suzuki and Sonogashira reactions in non-hazardous and sustainable deep eutectic solvents (DESs). The DES and catalyst were simply recycled five times with gradual slight decrease in the yield of the reactions. More importantly, the catalyst was magnetically isolated at the end of the recycling process. Overall, the utilization of DES as an environmentally friendly and recoverable reaction medium, as well as replacing the low-cost cobalt catalyst as an alternative to expensive Pd catalyst along with the facile catalyst isolation by employing an external magnetic field, make the present protocol promising from economic and green chemistry points of view for the clean C-C coupling reactions.
Pd–Ni bimetallic catalyst supported on dendrimer-functionalized magnetic graphene oxide for efficient catalytic Suzuki-Miyaura coupling reaction
Niakan, Mahsa,Masteri-Farahani, Majid
, (2022/01/26)
A novel type of dendritic structure was grown on the magnetic graphene oxide nanocomposite surface through thiol-ene click reaction. The resulting nanocomposite was utilized as a support for immobilizing Pd–Ni bimetallic nanoparticles, which were employed
Catalytic reduction of nitroarenes and Suzuki-Miyaura reactions using Pd complex stabilized on the functionalized polymeric support
Ariannezhad, Maryam,Esperi, Melika,Pourmorteza, Narges,Yousefi, Abed
, (2022/02/17)
The significance of aromatic amines as crude substances in diverse applications has attracted extensive consideration in the field of economic procedures for the reduction of nitroarenes. Also, the formation of Carbon–Carbon bond as a dominant step in the structure of complex molecules is an important phenomenon in chemical reactions. Improvements of eco-friendly methodologies for reduction process and Carbon–Carbon bond formation have been noticeable. The present work represents through a capable heterogeneous Pd catalyst, the reduction of nitroarenes to the corresponding amines in the presence of N2H4 as a weak hydrogen donor reagent in the room temperature and solvent-free condition was progressed. In addition, several C–C bond formations through Suzuki-Miyaura reaction using one-pot mixture containing aryl halide, arylboronic acid in the presence of Pd catalyst at refluxed condition proceeded. Furthermore, the reusability of Pd catalyst for both reduction and Suzuki reactions showed five successive runs without any significant loss in its activity.
Nickel-catalyzed reductive deoxygenation of diverse C-O bond-bearing functional groups
Cook, Adam,MacLean, Haydn,St. Onge, Piers,Newman, Stephen G.
, p. 13337 - 13347 (2021/11/20)
We report a catalytic method for the direct deoxygenation of various C-O bond-containing functional groups. Using a Ni(II) pre-catalyst and silane reducing agent, alcohols, epoxides, and ethers are reduced to the corresponding alkane. Unsaturated species including aldehydes and ketones are also deoxygenated via initial formation of an intermediate silylated alcohol. The reaction is chemoselective for C(sp3)-O bonds, leaving amines, anilines, aryl ethers, alkenes, and nitrogen-containing heterocycles untouched. Applications toward catalytic deuteration, benzyl ether deprotection, and the valorization of biomass-derived feedstocks demonstrate some of the practical aspects of this methodology.
Sustainable and recyclable magnetic nanocatalyst of 1,10-phenanthroline Pd(0) complex in green synthesis of biaryls and tetrazoles using arylboronic acids as versatile substrates
Bagherzadeh, Nastaran,Sardarian, Ali Reza,Eslahi, Hassan
, (2021/04/02)
A magnetic nanocatalyst was purveyed as a heterogeneous recoverable palladium-based catalyst anchored on green, sustainable and phosphine free support. Resulted Fe3O4@SiO2-Phen-Pd(0) nanocatalyst bearing powerful phenanthroline ligand was thoroughly characterized by physicochemical approaches like UV–vis, FT-IR, EDX, XRD, TGA, ICP, VSM, DLS, FESEM, and TEM analyses. After finding trustable data, the obtained magnetic catalyst was considered to be applied in the Suzuki-Miyaura type C-C couplings and getting corresponding tetrazoles using arylboronic acid derivatives as alternate precursors of aromatic halides and stupendous data were observed.
Green and sustainable palladium nanomagnetic catalyst stabilized by glucosamine-functionalized Fe3O4@SiO2 nanoparticles for Suzuki and Heck reactions
Eslahi, Hassan,Sardarian, Ali Reza,Esmaeilpour, Mohsen
, (2021/04/26)
A novel magnetic and heterogeneous palladium-based catalyst stabilized by glucosamine-functionalized magnetic Fe3O4@SiO2 nanoparticle was synthesized. The strategy relies on the covalently bonding of glucosamine to cyanuric chloride-functionalized magnetic nanoparticles followed by complexation with palladium. The structure of magnetic nanocatalyst was fully determined by FT-IR, XRD, DLS, FE-SEM, TEM, ICP, UV-Vis, TGA, VSM, and EDX. The obtained results confirmed that the palladium nanoparticles stabilized by glucosamine immobilized onto the magnetic support exhibited high activity in cross-coupling reactions of Suzuki-Miyaura and Mizoroki-Heck. Various aryl halides were coupled with arylboronic acid (Suzuki cross-coupling reaction) and olefins (Heck reactions) under the green conditions to provide corresponding products in high to excellent yields. Interestingly, the catalyst can be easily isolated from the reaction media by magnetic decantation and can subsequently be applied for consecutive reaction cycles (at least seven times) with no notable reduction in the catalytic activity.
Synthesis and characterization of Pd based on [2,2'- bipyridin]-4-amine functionalized nano cellulose as a novel and recyclable nano catalyst for Suzuki reaction
Mohammadnia, Majid,Sun, Yuqi
, (2020/06/29)
In this work, it was designed and prepared an efficient nanocatalyst Pd based on [2,2'- bipyridin]-4-amine functionalized nano cellulose (Pd?BPA?CNC) and then characterized by FT-IR, XRD, ICP-AES, EDX, SEM, TEM and TGA techniques. The catalytic activity of the nanocatalyst was investigated through one-pot synthesis of biaryl derivatives from the reaction of aryl halides with arylboronic acids in DMSO solvent conditions. This Simple and mild procedure displayed excellent recyclability and provided cleaner conversion in a short reaction time. All of these advantages make the protocol feasible and economical attractive for researchers.
Preparation and characterization of Cu supported on 2-(1H-benzo[d]imidazol-2-yl)aniline-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for Ullmann and Suzuki cross-coupling reactions
Danqing, Liang,Ming, Jin,Li, Li,Mohammadnia, Majid
, (2020/09/15)
Copper supported on 2-(1H-benzo[d]imidazol-2-yl)aniline (BIA)-functionalized Fe3O4 nanoparticles (Cu-BIA-Si-Fe3O4) as a novel magnetic catalyst was designed and used for the synthesis of new products via Ullmann and Suzuki cross-coupling reactions. The Ullmann reaction was performed by mixing arylboronic acid with aniline derivatives in dimethylsulfoxide solvent. Also, diaryls were synthesized via Suzuki C–C reactions between aryl halides and phenylboronic acid in the same solvent. The prepared materials and catalyst were characterized with various analytical techniques. The Cu-BIA-Si-Fe3O4 catalyst demonstrated catalytic efficiency with good to excellent yields for both types of reactions in comparison with commercial palladium catalysts. Also, the catalyst could be recovered by a simple filtration and retained its activity even after several cycles.
