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Relevant academic research and scientific papers

Amination of Aryl Halides Mediated by Electrogenerated Nickel from Sacrificial Anode

Electrochemical C(sp2)?N couplings mediated by nickel salts generated from the sacrificial anode has been described for the first time. In this approach, the sacrificial nickel anode is employed as the sole source of nickel and the process, operationally simple to set up, enables the preparation of functionalized arylamine derivatives with moderate to good yields, under mild reaction conditions and without additional ligand. A cooperative process between the two electrodes is involved in the proposed mechanism.

Product selective reaction controlled by the combination of palladium nanoparticles, continuous microwave irradiation, and a co-existing solid; ligand-free Buchwald-Hartwig aminationvs.aryne amination

We have developed a continuous microwave irradiation-assisted Buchwald-Hartwig amination using our original Pd nanoparticle catalyst with a copper plate as a co-existing metal solid. In this methodology, a microwave-controlled product selectivity was achieved between Buchwald-Hartwig amination and aryne amination performed under strongly basic conditions and at a high reaction temperature, because a polar chemical species such as Ar-Pd-halogen might be activated selectively by microwave radiation. Moreover, our catalyst could be used repeatedly over 10 times, and the amount of Pd leaching could be suppressed to a low level.

Pyrazolyl bistriazolyl phosphine compound and application of pyrazolyl bistriazolyl phosphine compound

The invention discloses a pyrazolyl bistriazolyl phosphine compound and application thereof. The invention discloses a compound shown as a formula I. In the formula I, R1 is hydrogen, C1-C6 alkyl or phenyl; R2 and R3 are phenyl; R4 and R5 are independently a C1-C6 alkyl group, a C3-C8 cycloalkyl group, or a phenyl group. The pyrazolyl bistriazolyl phosphine compound disclosed by the invention is stable in property, excellent in catalytic effect and high in selectivity, and can be applied to catalytic coupling of amine, boric acid compounds and halides.

Preparation method of pyrazole bistriazolylphosphine compound

The invention discloses a preparation method of a pyrazole bistriazolylphosphine compound. The invention discloses a preparation method of a compound as shown in a formula I. The preparation method comprises the following step: under the action of an alkali, carrying out a phosphonation reaction process as shown in the specification on a compound as shown in a formula II and a compound as shown ina formula III in a solvent in the presence of protective gas to obtain the compound as shown in the formula I, wherein R1 is hydrogen, a C1-C6 alkyl group or a phenyl group, R2 and R3 are phenyl, R4and R5 are independently a C1-C6 alkyl group, a C3-C8 cycloalkyl group or a phenyl group and x is halogen. The pyrazolyl bistriazolylphosphine compound obtained by the preparation method disclosed bythe invention is stable in property, excellent in catalytic effect and high in selectivity, and can be applied to catalytic coupling of amine, boric acid compounds and halides.

Nickel-Catalyzed Decarbonylative Amination of Carboxylic Acid Esters

The reaction of carboxylic acid derivatives with amines to form amide bonds has been the most widely used transformation in organic synthesis over the past century. Its utility is driven by the broad availability of the starting materials as well as the kinetic and thermodynamic driving force for amide bond formation. As such, the invention of new reactions between carboxylic acid derivatives and amines that strategically deviate from amide bond formation remains both a challenge and an opportunity for synthetic chemists. This report describes the development of a nickel-catalyzed decarbonylative reaction that couples (hetero)aromatic esters with a broad scope of amines to form (hetero)aryl amine products. The successful realization of this transformation was predicated on strategic design of the cross-coupling partners (phenol esters and silyl amines) to preclude conventional reactivity that forms inert amide byproducts.

Method for catalyzing nitro-arene and amine compound to be synthesized into aromatic amine compounds through palladium/imidazolium salt

The invention discloses a method for catalyzing nitro-arene and an amine compound to be synthesized into aromatic amine through palladium/imidazolium salt. The method comprises the steps that in an organic solvent, the palladium/imidazolium salt is taken as a catalyst, the nitro-arene and the amine compound are subjected to a coupling reaction under the function of alkali, and then the aromatic amine compounds are obtained through aftertreatment. The method is simple in ligand synthesis, storage is facilitated, the price is low, the use quantity of ligands is low, the yield of the product is high, and the substrates have high applicability and are suitable for preparing diarylamine and N-alkylated arylamine. The method can be used for synthesizing a series of aromatic amine compounds, andthe aromatic amine compounds have high application value in the fields of pesticides, medicines, materials and the like.

Well-Designed N-Heterocyclic Carbene Ligands for Palladium-Catalyzed Denitrative C-N Coupling of Nitroarenes with Amines

The C-N bond formation is one of the fundamental reactions in organic chemistry, because of the widespread presence of amine moieties in pharmaceuticals and biologically active compounds. Palladium-catalyzed C-N coupling of haloarenes represents one of the most efficient approaches to aromatic amines. Nitroarenes are ideal alternative electrophilic coupling partners, since they are inexpensive and readily available. The denitration and cross-coupling using nitroarenes as the electrophilic partners is challenging, because of the low reactivity of the Ar-NO2 bond toward oxidative addition. We report here the C-N coupling of nitroarenes and amines using palladium/5-(2,4,6-triisopropylphenyl)imidazolylidene[1,5-a]pyridines as the catalyst. The ligands are readily available from commercial chemicals. The reaction shows broad substrate scope and functional group tolerance. The method is applicable to both aromatic and aliphatic amines, and many secondary and tertiary aromatic amines bearing various functional groups were obtained in high yields.

Insights on bimetallic micellar nanocatalysis for buchwald-hartwig aminations

A nanocatalyst for micellar Buchwald-Hartwig aminations is developed, thoroughly characterized, and applied on a variety of substrates. The catalyst is stable under ambient conditions for at least six months. The catalyst retained its activity after several cycles, and its structure remained intact as confirmed by NMR spectroscopy. Association of Pd nanoparticles with Cu by a phosphine ligand is revealed by 31P NMR spectroscopy, and their linkage with the activated carbon surface is revealed by XAS analysis. Control NMR experiments revealed the binding of the ligand with both Cu and Pd, and all phosphine molecules are under the same environment. In addition to NMR and XAS analysis, the catalyst is characterized by SEM, HRTEM, XPS, and TGA. Reactions are highly reproducible at variable scales. Environmentally benign, proline-based amphiphile PS-750-M is critical for catalytic activity, which is achieved under mild conditions in water as the reaction medium. The inherent sustainability of these conditions coupled with a low E factor achievable through robust recycling of catalyst and reaction medium demonstrates the significant utility of this technology.

Practical Catalytic Cleavage of C(sp3)?C(sp3) Bonds in Amines

The selective cleavage of thermodynamically stable C(sp3)?C(sp3) single bonds is rare compared to their ubiquitous formation. Herein, we describe a general methodology for such transformations using homogeneous copper-based catalysts in the presence of air. The utility of this novel methodology is demonstrated for Cα?Cβ bond scission in >70 amines with excellent functional group tolerance. This transformation establishes tertiary amines as a general synthon for amides and provides valuable possibilities for their scalable functionalization in, for example, natural products and bioactive molecules.

Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines

Herein, we describe a new catalytic approach to accessing aromatic amines from an abundant feedstock, namely phenols. The most reliable catalytic method for converting phenols to aromatic amines uses an activating group, such as a trifluoromethane sulfonyl group. However, this activating group is eliminated as a leaving group during the amination process, resulting in significant waste. Our nickel-catalyzed decarboxylation reaction of aryl carbamates forms aromatic amines with carbon dioxide as the only byproduct. As this amination proceeds in the absence of free amines, a range of functionalities, including a formyl group, are compatible. A bisphosphine ligand immobilized on a polystyrene support (PS-DPPBz) is key to the success of this reaction, generating a catalytic species that is significantly more active than simple nonsupported variants.