5002-13-1Relevant articles and documents
Pseudo-Solid-State Suzuki–Miyaura Reaction and the Role of Water Formed by Dehydration of Arylboronic Acids
Pentsak, Evgeniy O.,Ananikov, Valentine P.
supporting information, p. 4239 - 4247 (2019/06/17)
Solvent-free reactions belong to a very attractive area of organic chemistry. The solvent-free Suzuki–Miyaura coupling is of special importance due to the problem of catalyst leaching in the presence of a solvent. This study investigates the course of reaction of solid aryl halides with arylboronic acids in the absence of a solvent and without any liquid additives. For the first time, a number of important conditions for performing a solid-state Suzuki–Miyaura reaction were analyzed in details. The results indicate a prominent role of water, which is formed as a by-product in the side reaction of arylboronic acid trimerization. Electron microscopy study revealed surprising changes occurring within the reaction mixture during the reaction and indicated the formation of spherical nano-sized particles containing the reaction product. Catalyst recycling was easily performed in the developed system and the product was isolated by sublimation, thus providing a possibility to completely avoid the use of solvents at all stages.
Mono-arylation method of dichlorobenzene compounds
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Paragraph 0024; 0026; 0028; 0029, (2018/05/16)
A mono-arylation method of dichlorobenzene compounds comprises the steps as follows: dichlorobenzene compounds shown in formula (I), arylboronic acid shown in formula (2), a N-heterocyclic carbene-palladium complex catalyst, an alkaline substance and a reaction solvent are mixed to react at 0-100 DEG C for 1-24 h under the protection of nitrogen, a reaction solution is subjected to posttreatment,and a mono-arylation product shown in formula (3) is obtained. A novel catalytic system is developed, the catalyst is stable and easy to obtain, the stable and cheap dichlorobenzene compounds can be subjected to the selective mono-arylation reaction, and the method has multiple advantages that the reaction operation is simple, the cost is low, the product is high in yield and purity and the like,is a brand-new method for synthesizing chloro-biphenyl compounds, provides a new synthesis route for the compounds and has good research value and industrial application prospects.
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 (2016/08/15)
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.