N-Arylation of carbazole by microwave-assisted ligand-free catalytic CuI reaction

N-Arylation of carbazole has been achieved in high yields within 1 h using a microwave-assisted catalytic CuI reaction with no organic ligand. The N-arylation can be performed by various arylhalides, such as phenyl, pyridine, thiophene, and thiazole moieties. Specifically, N-arylated bromocarbazoles were converted into useful synthetic intermediates for functionalized carbazole materials.     

1, 1'-Binaphthyl-2, 2'-diamine Dihydrochloride: an Efficient Ligand for the N-Arylation of Imidazole with Aryl/heteroaryl Halides Catalyzed by CuI

Employing 1,1'-binaphthyl-2,2'-diamine(BINAM) dihydrochloride as an efficient and commercially available ligand, relatively mild and highly efficient copper-catalyzed coupling reactions of imidazole with aryl and heteroaryl halides have been developed. Various N-arylimidazoles could be synthesized in moderate to excellent yields.     

One‐Pot Ullmann C–N Coupling Cyclization Toward Domino Synthesis of Fused Hexacyclic Quinolinotriazoloacridinones Catalyzed by CuI/L‐Proline

A one‐pot method for consecutive Konoevenagel condensation, Michael addition, cyclization, dehydrogenation, and Ullmann coupling of 2‐halogenated aromatic aldehyde, 1H‐benzo[d ][1,2,3]triazol‐5‐amine, and cyclohexane‐1,3‐diones is presented. This procedure provided an efficient synthesis of fused hexacyclic quinolinotriazoloacridinone derivatives in good yields catalyzed by CuI/L‐proline.     

Domino synthesis of fused hexacyclic imidazoquinolinoacridinones catalyzed by CuI/l-proline

A three-component reaction of 2-halogenated aromatic aldehydes, 1H-benzo[d]imidazol-5-amine and cyclohexane-1,3-diones is described, and gives imidazoquinolinoacridinone derivatives in good yields catalyzed by CuI/l-proline. This Domino reaction constructs a fused hexacyclic skeleton in one-pot containing two new rings, six new bonds and an Ullmann-type C–N bond coupling reaction.     

A general and efficient CuI/BtH catalyzed coupling of aryl halides with thiols

We report an exceptionally mild, general and efficient copper catalyzed cross coupling reaction of aryl bromides and thiols using 0.5 mol % CuI and 1 mol % benzotriazole. Experimental simplicity, generality, functional group tolerance and low cost of the catalyst are advantages of the protocol.     

Recent Progress Concerning the N-Arylation of Indoles

This review summarizes the current state-of-the-art procedures in terms of the preparation of N-arylindoles. After a short introduction, the transition-metal-free procedures available for the N-arylation of indoles are briefly discussed. Then, the nickel-catalyzed and palladium-catalyzed N-arylation of indoles are both discussed. In the next section, copper-catalyzed procedures for the N-arylation of indoles are described. The final section focuses on recent findings in the field of biologically active N-arylindoles.     

CuI/Dabco as a highly active catalytic system for the Heck-type reaction

An efficient catalytic system using CuI/Dabco (triethylenediamine) for the Heck-type cross-coupling reaction was developed. In the presence of 10 mol % of CuI and 20 mol % of Dabco, the coupling of various aromatic iodides and 1-((Z)-2-bromovinyl)benzene with olefins was carried out efficiently and selectively to afford the corresponding internal olefins in moderate to good yields.     

Amination Reactions of Aryl Halides with Nitrogen‐Containing Reagents Catalyzed by CuI in Ionic Liquid

CuI‐catalyzed coupling reactions of aryl iodides and electron‐deficient aryl bromides with nitrogen‐containing reagents, such as imidazole, benzimidazole, aliphatic primary and secondary amines, aniline, primary and secondary amides, in ionic liquid were developed. The reaction conditions involved the use of [Bmim][BF₄] as the solvent, potassium phosphate as the base, and CuI as the catalyst. The CuI and [Bmim][BF₄] could be recovered and recycled for five consecutive trials without significant loss of their activity.     

CuI/TMEDA催化合成芳基葡萄糖碳苷化合物

以THF为溶剂, CuI/TMEDA为催化剂,四乙酰溴代葡萄糖与芳基溴化镁经取代反应合成了芳基葡萄糖碳苷（2a~2c）,其结构经¹H NMR和¹³C NMR确证。该方法立体选择性较好。在最佳反应条件(THF为溶剂,10% CuI和10% TMEDA为催化剂,于0 ℃反应至终点)下,2a~2c的收率为58%~71%, α/β为1/6.5~1/7.1。     

CuI/l-proline catalyzed click reaction in glycerol for the synthesis of 1,2,3-triazoles

Despite the apparent simplicity of the copper(I) iodide catalyzed CuAAC reaction, the conversion of the catalytic species, i.e. Cu(I) to thermodynamically more stable Cu(II), via aerial oxidation or disproportionation is a major issue. To stabilize the Cu(I) species, the reaction is ideally carried out under an inert atmosphere in the presence of additives such as alcohols, amines, thiols, and aldehydes. Herein, we report the first CuI catalyzed click reaction without an inert atmosphere by employing the CuI/l-proline system in glycerol. The method showed remarkable stability towards sensitive functional groups such as acetonides and 1,2,4-trioxanes.     

N‐Arylation of Heterocycles Promoted by Cyclen Derivatives

An efficient copper‐catalyzed N‐arylation reactions of imidazole, indole, and triazole with aryl or heteroaryl halides using cyclen derivatives as efficient organic base and ligand at moderate temperature have been investigated. The cross‐couplings proceed smoothly with good to excellent yields.     

Proline-catalyzed asymmetric assembly reactions: enzyme-like assembly of carbohydrates and polyketides from three aldehyde substrates

Directed asymmetric assembly of simple achiral building blocks into stereochemically complex molecules like triketides has been described for the first time using l-proline catalyzed asymmetric double aldol reactions. The product pyranoses contain four asymmetric centers constructed under proline catalysis in a highly diastereoselective and modestly enantioselective fashion from three aldehyde molecules. These results suggest that the construction of complex products from simple starting materials is within the realm of organocatalysis involving the simple naturally occurring amino acid l-proline. Our successful assembly of pyranoses from simple aldehydes under proline catalysis suggests that this approach may warrant consideration as a prebiotic route to sugars and polyketides.     

CuI-catalyzed Synthesis of Aryl Thiocyanates from Aryl Iodides

Aryl thiocyanates are important compounds not only for their interesting biological properties, but also because of their use as a versatile starting material for many sulfur- containing aromatic compounds, including sulfonyl cyanides, sulfonic acids, sul…     

CuI/iodine-mediated homocoupling reaction of terminal alkynes to 1,3-diynes

A facile and efficient pathway for CuI/iodine-mediated homocoupling reaction of terminal alkynes to symmetrical 1,4-disubstituted 1,3-diynes in good to excellent yields was reported.     

Direct N‐Arylation of Azaheterocycles with Aryl Halides under Ligand‐free Condition

A simple and efficient C? N cross‐coupling method of aryl halides with various heterocycles was reported, by using 10 mol% of CuI as catalyst and 1.2 equiv. NaH as base. Aryl iodides, aryl bromides and many substituted aryl chlorides could efficiently react with heterocycles, providing variety of N‐arylated products in good to excellent yields. The ligand‐free catalyst system was stable in air and could be readily reused.     

CuI/TPA/4-乙酰胺基-TEMPO催化的苄醇与烯丙基醇氧化反应的研究

CuI/TPA(tris(pyridin-2-ylmethyl)amine)/4-乙酰胺基-TEMPO(2,2,6,6-Tetramethylpiperidyl-1-oxyl)催化体系能够在室温下,以氧气作氧化剂,乙腈作溶剂,高效、高选择性地催化一系列苄醇,烯丙基醇和含杂原子伯醇的氧化,且在体系中无需添加任何碱作助催化剂.     

Study of CuI catalyzed coupling reactions of aryl bromides with imidazole and aliphatic amines under microwave dielectric heating

Amination of a variety of functionalized aryl bromides with imidazole and primary and secondary amines was accomplished using a CuI/amino acid catalyst system under microwave heating. Application of microwave irradiation shortened the reaction time from 25–40 h to 6–20 min. Good to very good yields of the corresponding coupling products were obtained when imidazole and secondary amines were used as starting materials. In case of primary amines, the outcome of the reaction was dependent on the character of the substituent on aryl bromide.     

N-Arylation of 3-Formylquinolin-2(1H)-ones Using Copper(II)-Catalyzed Chan–Lam Coupling

3-formyl-2-quinolones have attracted the scientific community’s attention because they are used as versatile building blocks in the synthesis of more complex compounds showing different and attractive biological activities. Using copper-catalyzed Chan–Lam coupling, we synthesized 32 new N-aryl-3-formyl-2-quinolone derivatives at 80 °C, in air and using inexpensive phenylboronic acids as arylating agents. 3-formyl-2-quinolones and substituted 3-formyl-2-quinolones can act as substrates, and among the products, the p-methyl derivative 9a was used as a substrate to obtain different derivatives such as alcohol, amine, nitrile, and chalcone.     

用环加成反应合成含氟杂环化合物的研究

综述了近年来利用一些新型的含氟砌块，通过它们的环加成反应来高效地合成 含氟杂环化合物的研究，其中包括以下两个部分：(1)用1，3—偶极环加成反应合 成五元含氟杂环化合物；(2)用杂原于Diels-Alder反应合成六元含氟杂环化合物．