19287-62-8

Upstream product

• 13029-09-9 2,2'-dibromobiphenyl 
• 108-44-1 1-amino-3-methylbenzene 
• 625-95-6 3-Iodotoluene 
• 86-74-8 9H-carbazole 
• 108-41-8 1-chloro-3-methylbenzene 

Relevant academic research and scientific papers

Visible Light-Mediated Ullmann-Type C-N Coupling Reactions of Carbazole Derivatives and Aryl Iodides

The combined use of an iridium-based photocatalyst and a copper salt under blue light emitting diode irradiation enables the Ullmann-type C-N cross-coupling reaction between carbazole derivatives and aryl iodides to proceed under mild conditions.

Microenvironment modulation of cuprous cluster enables inert aryl chlorides activation in single-molecule metallaphotoredox amination

Amination of aryl halides is an important tool in organic synthesis and the activation of inert aryl chlorides is particular difficult. We herein report the first study of aromatic microenvironment modulation of cuprous clusters as single-molecule metalla

Method for synthesizing carbazole derivative

The invention aims to provide a method for synthesizing a carbazole derivative. The method is characterized in that palladium chloride is used as a catalyst, 2, 2' - dibromobiphenyl is used as an electrophilic reagent, primary amine is taken as a nucleophile, and the carbazole derivative is directly cross-coupled under the conditions of toluene as a solvent and an air atmosphere. The method has the advantages of high yield, high selectivity, simplicity and convenience in operation and the like.

Scope, Kinetics, and Mechanism of “On Water” Cu Catalysis in the C–N Cross-Coupling Reactions of Indole Derivatives

A simple and cost-effective protocol for the C–N cross coupling of indole derivatives with aryl iodides using CuI/phenanthroline catalytic system in aqueous and DME/H2O solvent mixture is described. The reactions were performed in the absence of phase-transfer catalyst, and afforded N-arylated products in moderate to excellent yields under mild reaction conditions. A systematic tuning of reaction conditions using DME as a co-solvent enables to improve product yields of N-arylation reactions. The broad substrate scope, easy performance, and low loading of catalyst as well as ligand render this approach appropriate for large scale processes. The mechanism of “on water” Cu-catalyzed N-arylation reaction is investigated using kinetic and computational studies, which reveal interesting mechanistic aspects of the reaction. A series of kinetic experiments showed significant rate enhancement for “on water” Cu-catalyzed N-arylation over the reaction performed in the organic solvent (DME). Computational studies corroborated “on water” rate acceleration by delineating the role of water in the reaction. The water induces rate acceleration by stabilizing the transition state of oxidative addition through hydrogen bonding interactions, presumably at the oil-water interface, and thus helps to reduce the free energy of activation of oxidative addition of iodobenzene to the Cu complex, which is identified as the rate-limiting step of reaction.

Copper/β-diketone-catalysed N-arylation of carbazoles

A copper-catalysed C-N bond-forming reaction of carbazoles with aryl iodides is described. Several commercially available ligands such as β-diketone and diamine, are tested in the N-arylation of carbazoles. The catalytic system generated in situ from an inexpensive copper salt, simple β-diketone and inorganic base efficiently N-arylated the carbazoles. A wide range of aryl iodides and carbazoles can be coupled to generate N-arylcarbazoles in the presence of various functional groups. However, the sterically hindered effect of aryl iodides is evident in this catalytic system. The selectivity of two iodine atoms on the aromatic ring of diiodobenzene is evaluated in the developed catalytic system. Results showed that the selectivity of diiodobenzene can be tuned by the reaction temperature.

An Efficient Synthesis of N-(Hetero)arylcarbazoles: Palladium-Catalyzed Coupling Reaction between (Hetero)aryl Chlorides and N-Carbazolylmagnesium Chloride

An efficient method for the synthesis of N-(hetero)arylcarbazoles, useful compounds for functional materials, is reported. Various (hetero)aryl chlorides reacted with N-carbazolylmagnesium chloride in the presence of a palladium catalyst (0.05 to 0.2 mol%) prepared from allylpalladium(II) chloride dimer {[PdCl(allyl)]2} and di-tert-butyl(2,2-diphenyl-1-methylcyclopropan-1-yl)phosphine (cBRIDP) under mild conditions (110°C) in a short period of time (15 min to 2 h) to give N-(hetero)arylcarbazoles in high yields. The reactions of bromochlorobenzenes proceeded in favour of the bromo group to afford N-(chlorophenyl)carbazoles in a highly selective manner. Functional materials for use in organic light-emitting diodes, such as mCP, 26mcPy, CBP and TCB, were also obtained in high yields within 15 min by the reaction of (hetero)aryl polyhalides. Optimization of the reaction conditions and a postulated catalytic cycle for the reaction are also discussed.

PROCESS FOR PRODUCING N-(HETERO)ARYLAZOLES

The present invention provides a process for effectively producing an N-(hetero)arylazole with high yield, which is useful as a medical or agrochemical product, an organic photoconductor material, an organic electroluminescent element material, or the like. The present invention relates to a process for producing an N-(hetero)arylazole, which includes reacting a (hetero)aryl (pseudo)halide with an NH-azole in the presence of: a catalyst including a palladium compound and a coordination compound; and a basic magnesium compound.