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A new and efficient approach for the N-arylation of 8-aminoquinoline amides with diaryliodonium salts has been developed. This chelation-assisted selective C-N cross-coupling reaction gave the desired N-arylated 8-aminoquinoline in moderate to good yields

In the present study, we report the synthesis of a series of copper(II) complexes with a wide range of ligands and their testing in the copper catalyzed Chan-Evans-Lam (CEL) coupling of aniline and phenylboronic acid. The efficiency of the coupling was directly connected with the ease of the reduction of Cu(II) to Cu(I) of the complexes. The most efficient catalyst was derived from 4-t-butyl-2,5-bis[(quinolinylimino)methyl]phenolate and two Cu(II) ions. Depending on the counter-anion nature and the concentration of the reaction mixture, the reaction can be directed to predominant C?N-bond formation. Forty-three derivatives of diphenylamine were prepared under the optimized conditions. The proposed mechanism of the catalysis was based on the reduction potential of a series of complexes, molecular weight measurements of the catalytic complex in MeOH and the kinetic studies of aniline and phenylboronic acid coupling. In addition, an 1H NMR experiment in a sealed NMR tube, without external oxygen supply available, proved that no complete Cu(II) to Cu(I) conversion was observed under the condition, ruling out the usually accepted mechanism of the C?N coupling, which included the oxygenation of the intermediately formed Cu(I) complexes after the key step of C?N conversion had already been completed. Instead, a mechanism was proposed, involving an oxygen molecule coordinated to two copper ions in the key C?N bond formation without any detectable conversion of the Cu(II) complexes to Cu(I).

PURPOSE: A compound for an electronic element, an electronic element using the same, and an electronic device thereof are provided to improve light emitting efficiency, thermal resistance, color purity, and lifetime and to lower driving voltage using indoloquinoxaline derivatives. CONSTITUTION: A compound of an organic electronic element contains a compound of chemical formula 1. The organic electronic element has one or more organic layers containing the compound. The organic electronic element comprises a first electrode, the organic layers, and a second electrode. The organic layers are selected among a light emitting layer, a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer. An electronic device comprises a display device with the organic electronic element; and a control unit which drives the display device.

A simple and efficient method for transition-metal-free N-arylation of various amines by triarylsulfonium triflates is described. Both aliphatic and aromatic amines were smoothly converted at 80 °C in the presence of tBuOK or KOH to give the corresponding mono N-arylated products in good to high yields. The molar ratios of the reactants and the choice of bases had a big effect on the reaction. When a large excess of [Ph3S][OTf] and tBuOK were employed for primary amines under the standard conditions, the bis(N-phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N-phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N-arylated products when using 4-substituted triarylsulfonium triflates suggested that the reaction might proceed through an aryne intermediate. The present protocol demonstrated that triarylsulfonium salts are versatile arylation reagents in the construction of CAr?N bonds.

An efficient and general selective method for the synthesis of 8-aminoquinoline derivatives has been disclosed through transition metal direct C–N coupling from fluoroquinolines and arylamines. Significantly, good chemo- and regio-selectivity was observed

The invention discloses a method for synthesis of quinoline-8-amine and derivatives thereof from fluoroquinolines, and belongs to the technical field of organic synthesis. The quinoline-8-amine and the derivatives thereof are prepared from fluoroquinoline compounds and aromatic amines compounds as a substrate in the presence of solvent toluene and hydrides by synthesizing reaction. The method is simple in operation and suitable for industrial production. The raw materials needed for the synthesis are cheap, the cost of the synthesis is low, and a variety of amino quinoline derivatives can be synthesized by the simple and single method.

An efficient solvent-free protocol for the Buchwald-Hartwig cross-coupling reaction of aryl and heteroaryl chlorides with primary and secondary amines using the Pd(dba)2/ligand 1 catalytic system has been developed. Notably, the catalytic system also efficiently catalyzed the reaction under aqueous conditions.

The invention relates to a preparation method of N-phenyl-8-aminoquinoline and belongs to the technical field of organic chemical synthesis. The preparation method of the N-phenyl-8-aminoquinoline is characterized by comprising the following steps: reacti

The synthesis of a novel mesoporous covalent imine polymeric (MCIPs) material, involving simple Schiff-base chemistry, is reported. This highly functionalised nitrogen-rich material acts as a good support for immobilising CuII ions, exhibiting excellent catalytic activity in promoting the Chan-Lam cross-coupling reaction between biologically active amines and arylboronic acids. The performance of this catalyst is also evident from its broad substrate scope, high stability, real heterogeneity, mild reaction conditions and reusability without loss of activity. The observed results will provide additional scope on the design and catalytic applications of this emerging class of materials.

Herein, we disclose the metal-free synthesis of arylamines via the direct amination of phenols using aminating reagents. This reaction procedure uses easy accessible aminating reagents and provides a versatile synthetic route to a broad range of arylamines with various functionalities in good to excellent yield. By using a two-step route of amination and oxidative coupling reaction, we synthesized three naturally occurring carbazole alkaloids: murrayafoline A, mukonine, and clausenine from two commercially available phenols. Georg Thieme Verlag Stuttgart · New York.

The present invention provides novel compounds and ligands that are useful in transition metal catalyzed cross-coupling reactions. For example, the compounds and ligands of the present invention are useful in palladium or gold catalyzed cross-coupling reactions.

The syntheses of 2-(di-tertbutylphosphino)-N,N-dimethylaniline (L1, 71%) and 2-(di-1-adamantylphosphino)-N,N-dimethylaniline (L2, 74%), and their application in BuchwaldHartwig amination, are reported. In combination with [Pd(allyl)Cl]2 or [Pd(cinnamyl)Cl]2, these structurally simple and air-stable P,N ligands enable the cross-coupling of aryl and heteroaryl chlorides, including those bearing as substituents enolizable ketones, ethers, esters, carboxylic acids, phenols, alcohols, olefins, amides, and halogens, to a diverse range of amine and related substrates that includes primary alkyl- and arylamines, cyclic and acyclic secondary amines, N-H imines, hydrazones, lithium amide, and ammonia. In many cases, the reactions can be performed at low catalyst loadings (0.5-0.02 mol % Pd) with excellent functional group tolerance and chemoselectivity. Examples of cross-coupling reactions involving 1,4-bromochlorobenzene and iodobenzene are also reported. Under similar conditions, inferior catalytic performance was achieved when using Pd(OAc)2, PdCl2, [PdCl2(cod)] (cod = 1,5-cyclooctadiene), [PdCl 2(MeCN)2], or [Pd2(dba)3] (dba = dibenzylideneacetone) in combination with L1 or L2, or by use of [Pd(allyl)Cl]2 or [Pd(cinnamyl)Cl]2 with variants of L1 and L2 bearing less basic or less sterically demanding substituents on phosphorus or lacking an ortto-dimethylamino fragment. Given current limitations associated with established ligand classes with regard to maintaining high activity across the diverse possible range of C-N coupling applications, L1 and L2 represent unusually versatile ligand systems for the cross-coupling of aryl chlorides and amines

The novel N-R-quinolinyl-8-amino ligands HL1-5 (R = 2,6-Me 2C6H3 (HL1), 2,4,6-Me 3C6H2 (HL2), 2,6-Et 2C6H3 (HL3), 2,6-iPr 2C6H3 (HL4), C6H 5 (HL5)) reacted with Sc(CH2SiMe 3)3(THF)2 to afford the well-defined complexes (L1-5)Sc(CH2SiMe3)2(THF) (1-5), which were fully characterized by NMR spectral and X-ray diffraction analyses. Complexes 1-3 combined with organoborates to establish binary systems that exhibited high activity for the polymerization of styrene, while 4 was less active and 5 was almost inert. The cationic complex [L1Sc(CH 2SiMe3)(DME)2][B(C6F 5)4] (6) was successfully isolated by treatment of 1 with [PhMe2NH][B(C6F5)4], and represents probably the structural model of the initiation active species. Remarkably, upon addition of aluminum trialkyls to the binary systems, distinguished improvement in catalytic performances was achieved, among which the ternary system 1/5AliBu3/[Ph3C][B(C6F 5)4] displayed the highest activity (1.56 - 106 g mol-1 h-1) and syndioselectivity (r = 0.94) via a chain-end control mechanism governed by the concerted steric effect of the ligand and the aluminum alkyls. This represents the first non-cyclopentadienyl stabilized rare-earth metal based catalyst showing both high activity and specific selectivity for the polymerization of styrene, which might shed new light on designing more efficient precursors and further investigation of the mechanism for this polymerization.

1-Aminonaphthalenes and 5-and 8-aminoquinolines were rapidly prepared from the respective aryl bromides in good yields by Pd-catalyzed aryl amination under microwave conditions. Consistent improvements in yields over those obtained under standard conditions were seen with quinoline substrates. In the cases where 5-bromo-8-cyanoquinoline was used as a substrate, no desired products were obtained under standard conditions with a number of different primary and secondary amines. However, microwave conditions provided the desired products in good to excellent yields.