Diaryliodonium salts are an important part of hypervalent iodine chemistry, owing to their highly electrophilic character, non-toxicity, and air and moisture stability, have been identified as an important arylating agent. It has been widely applied...
Phenylazocarboxylate is described as a novel non-organometallic aryl nucleophile in palladium-catalyzed arylation.
We describe a mechanism-guided discovery of a synthetic methodology that enables the preparation of aromatic amides from 2-bromo-2,2-difluoroacetamides utilizing a copper-catalyzed direct arylation. Readily available and structurally simple aryl prec...
Direct arylation is an atom-economical alternative to more established procedures such as Stille, Suzuki or Negishi arylation reactions. In comparison with other palladium sources and ligands, the use of palladium pincer complexes as catalysts or pre...
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 ni...
Various aryl-substituted purine derivatives were synthesized through the direct arylation of halopurines with aromatic compounds, facilitated by the combination of triflic acid and fluoroalcohol. This metal-free method is complementary to conventiona...
Palladium(II) acetate, in combination with triphenylphosphine, catalyzes direct arylation of 1,4-disubstituted 1,2,3-triazoles effectively. This C–H arylation reaction provides facile access to fully substituted triazoles with well-defined regiochemi...
Commercially available copper and copper (II) oxide nanoparticles (CuNPs and CuO NPs) were characterized using TEM and electronography methods to elucidate their true average size and composition. The catalytic amine arylation using unsupported coppe...
The C3 direct arylation of 1H-indazole and 1H-7-azaindazole has been a significant challenge due to the lack of the reactivity at this position. In this paper, we describe a mild and an efficient synthesis of new series of C3-aryled 1H-indazoles and...
The use of potassium tert-butoxide as the base in arylation reactions of an enollactone with a series of benzyl halides was explored. Our work demonstrates that the ratio of C-arylation to O-arylation varies with the substitution pattern of the aryl...
In recent years, small molecular acceptors (SMAs) have extensively promoted the progress of organic solar cells (OSCs). The facile tuning of chemical structures affords SMAs excellent tunability of their absorption and energy levels, and it gives SMA...
CuO/AB was found to be a simple and efficient catalyst for the N-arylation of a variety of nitrogen-containing heterocycles, giving the products in excellent yields.
Ullmann-type C–N heterocoupling reactions have been applied for the syntheses of N-arylated amines. In the past decade, transition metal-catalyzed N-arylations have been recognized as particularly efficient procedures for the preparation of nit...
Direct C-H arylation coupling is potentially a more economical and sustainable process than conventional cross-coupling. However, this method has found limited application in the synthesis of organic dyes for dye-sensitized solar cells. Although dire...
Apart from carbon atoms, some cyclic molecules contain other elements and play an extraordinary role in human life. Among these systems, 1,3,4-oxadiazole derivatives deserve special attention due to their biological properties such as antibacterial,...
Copper-catalyzed Csp2–Csp2 bond forming reactions through C–H activation are still one of the most useful strategies for the diversification of heterocyclic moieties using various coupling partners. A catalytic protocol for the C–H...
In this contribution, an eco-friendly, sustainable, and efficient palladium nanoparticle-decorated chitosan (Pd@Chitosan) catalyst was synthesized by a simple impregnation method. The synthesized material was utilized as a heterogeneous catalyst for...
The 1,3-oxazolidine-2-thiones (OZTs) are important chiral molecules, especially in asymmetric synthesis. These compounds serve as important active units in biologically active compounds. Herein, carbohydrate anchored OZTs were explored to develop a c...
Rapid development of the copper-catalyzed amination of aryl halides in the beginning of the 21st century, known as the Renaissance of the Ullmann chemistry, laid foundations for the use of this method as a powerful tool for the construction of the C(...
Owing to the pioneering works performed on the metal-catalyzed sp2 C–H arylation of indole and pyrrole by Sanford and Gaunt, N– and C-arylation involving diaryliodonium salts offers an attractive complementary strategy for the late-stage...
The palladium-catalyzed direct arylation of azoles with (hetero)aryl halides is nowadays one of the most versatile and efficient procedures for the selective synthesis of heterobiaryls. Although this procedure is, due to its characteristics, also of...
A series of new benzimidazolium halides were synthesized in good yields as unsymmetrical N-heterocyclic carbene (NHC) precursors containing the N–CH2–arene group. The benzimidazolium halides were readily converted into ruthenium(II)–NHC complexes wit...
(S)-N-methylpyrrolidine-2-carboxylate, a derivative of natural L-proline, was found to be an efficient ligand for the copper-catalyzed Goldberg-type N-arylation of amides with aryl halides under mild conditions. A variety of N-arylamides were synthes...
Transition-metal-free direct arylation of C-H or N-H bonds is one of the key emerging methodologies that is currently attracting tremendous attention. Diaryliodonium salts serve as a stepping stone on the way to alternative environmentally friendly a...
The palladium-catalyzed cross-coupling reaction used for carbon–carbon bond formation is one of the most commonly applied reactions in modern organic synthesis. In this work, a concise strategy was developed for constructing the tetrahydroisoqu...
We report a green and efficient visible-light-driven method for the arylation and alkylation of quinoxalin-2(1H)-ones and quinolines. This catalyst-free process utilizes air as the oxidant, offering mild reaction conditions, environmental sustainabil...
A novel and simple HCl-mediated, photocatalytic method for quinoxaline(on)es C3-H arylation with arylhydrazine under transition metal catalyst- and oxidant-free conditions is presented. Various quinoxaline(on)es underwent this transformation smoothly...
Efficient and general protocols for the O-tert-boc protection and O-arylation of phenols were developed in this paper using a recyclable magnetic Fe3O4-Co3O4 nanocatalyst (Nano-Fe-Co), which is easily accessible via simple wet impregnation techniques...
3-Aryl-2-chloropropylisothiocyanates (1) are formed by interaction of arenediazonium chlorides with allyl isothiocyanate. Adducts 1 react with monoacylhydrazines to form 1-acyl-4-(3-aryl-2-chloropropyl)thiosemicarbazides (2a–d). Thiosemicarbazides 2a...
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-catalyz...
NOBIN and BINAM derivatives harboring biaryl frameworks are recognized as a class of important atropisomers with versatile applications. Here, we present an efficient synthetic route to access such compounds through copper-catalyzed domino arylation...
In this work, a new n-type polymer based on a thiazole-diketopyrrolopyrrole unit has been synthesized through direct (hetero)arylation polycondensation. The molar mass has been optimized by systematic variation of the the monomer concentration. Optic...
Visible-light-active, organic, heterogeneous photocatalysts offer an ecologically friendly and sustainable alternative to traditional metal-based catalysts. In this work, we report the microwave synthesis of nanocarbon dots (CDs), loaded with graphit...
The development of a mild, general, and green method for the C-H arylation of pyrazoles with relatively unreactive aryl halides is an ongoing challenge in organic synthesis. We describe herein a novel sonophotoreactor based on an ultrasonic cleaning...
Pyranoquinolinones synthesized from citral were used for Cu-catalyzed N-arylation with a wide range of arylboric acids. The reaction proceeded well with a broad substrate scope, providing a direct way to access highly functional pyranoquinolinone cor...
In this paper, a simple and clean process for the alkylation and arylation of nitrogen-containing heterocycles is reported. The reactions were conducted using the Q-tube® as a non-conventional technology, in water as a green solvent, at overboiling t...
A series of C2-symmetric chiral benzimidazolium salts, the precursor of N-heterocyclic carbene ligands, were designed and synthesized from 1,2-dibromobenzene. In situ prepared corresponding carbenes were tested in the asymmetric palladium-catalyzed i...
Pd-catalyzed regioselective C–H arylation is a useful tool for the chemical modification of aromatic heterocycles and 2-arylbenzofuran derivatives are of interest as biologically active substances. Herein, the reaction of triarylantimony difluo...
π-conjugated macromolecules for organic polymeric solar cells can be rationally engineered at the molecular level in order to tune the optical, electrochemical and solid-state morphology characteristics, and thus to address requirements for the effic...
An efficient palladium-catalyzed carbonylation of aryl fluorosulfates with aryl formates for the facile synthesis of esters was developed. The cross-coupling reactions proceeded effectively in the presence of a palladium catalyst, phosphine ligand, a...
A rapid, efficient, and original synthesis of novel pyrido[3,2,1-de]phenanthridin-6-ones is reported. First, the key cinnamamide intermediates 8a–f were easily prepared from commercial substituted anilines, cinnamic acid, and 2-bromobenzylbromi...
Aryl- and heteroaryl units are present in a wide variety of natural products, pharmaceuticals, and functional materials. The method for reduction of aryl halides with ubiquitous distribution is highly sought after for late-stage construction of vario...
Iodine-methanol mediated oxidative-aromatization of 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones afforded the corresponding 2-aryl-6,8-dibromo-4-methoxy-quinolines in high yield and purity. The isomeric 1-(2-amino-3,5-dibromophenyl)-3-aryl-2-pro...
The interest in the NLO response of organic compounds is growing rapidly, due to the ease of synthesis, availability, and low loss. Here, in this study, Cu(II)-catalyzed selective N-arylation of 2-aminobenzimidazoles derivatives were achieved in the...
This paper reports the synthesis of D-A polymers containing 1,2-dithienylethene (DTE) units via palladium-catalyzed direct arylation polymerization (DArP). The reaction of dibromoisoindigo (1-Br) and DTE (2-H), in the presence of Pd2(dba)3·CHC...
Palladium-catalyzed direct (het)arylation reactions of strongly electron-withdrawing tricyclic benzo[1,2-d:4,5-d′]bis([1,2,3]thiadiazole) and its 4,8-dibromo derivative were studied; the conditions for the selective formation of mono- and bis-a...
NiCp†L(NHC)](+) complexes (Cp† = Cp (η5-C5H5), Cp* (η5-C5Me5); NHC = N-heterocyclic carbene; L = Cl− or NCMe) have been tested as pre-catalysts for the direct arylation of benzothiazole in the presence of an alkoxide. Only...
Under aqueous conditions, transition-metal catalysis offers an attractive platform for greener C–N bond formation by reducing reliance on hazardous organic solvents. Herein, we report a microwave-assisted palladium-catalyzed selective N-arylati...
A new, simplified method for the synthesis of dimethyl aryl acylsulfonium salts has been developed. A series of dimethyl aryl acylsulfonium bromides were prepared by the reaction of aryl methyl ketones with hydrobromic acid and dimethylsulfoxide (DMS...
Direct (hetero)arylation (DHA) is playing a key role in improving the efficiency and atom economy of C–C cross coupling reactions, so has impacts in pharmaceutical and materials chemistry. Current research focuses on further improving the gener...
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