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...
Aryl halides are important intermediates for chemical synthesis. However, the negative reduction potential up to −2.7 V (vs. SCE) makes photoredox conversion of aryl halides by reductive dehalogenation to aryl radicals for chemical transformati...
Nickel-catalyzed cyanation of aryl halides has emerged as a powerful and sustainable method for the synthesis of aryl nitriles—valuable motifs widely found in pharmaceuticals, agrochemicals, and functional materials. Compared to traditional cya...
The search for economic alternatives in the use of expensive scientific equipment represents a way of providing many laboratories access to scientific developments that, otherwise, might be hampered by economic constraints. This inspired the purpose...
We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g...
The present work describes the synthesis of mono- and bis-pyrazole compounds bearing flexible p-tolyl ether and rigid 4,5-dibromo-2,7-di-tert-butyl-9,9-dimethyl-9H-xanthene backbones as pyrazolyl analogues of DPEphos and Xantphos ligands, respectivel...
The fabrication of low-dimensional nanostructures through on-surface synthesis has emerged as a promising strategy for developing high-precision electronic devices. Among various reactions, Ullmann-type coupling (with carbon–halogen bond activa...
In this study, we present a straightforward and highly effective photo-triggered hydrogenation method for aryl halides, devoid of transition-metal catalysts. Through the synergistic utilization of light, PhNHNH2, and a base, we have successfully init...
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(...
A simple procedure for the palladium-catalyzed cyanation of aryl halides is described via a nucleophilic non-toxic cyanide source, K4[Fe(CN)6] in the presence of Pd/coral reef nanocomposite as a heterogeneous catalyst; the protocol provides a useful...
The direct formation of (hetero)biaryls from readily available (hetero)aryl halides under mild reaction conditions can be efficiently achieved through the Masuda borylation–Suzuki coupling (MBSC) sequence. The MBSC sequence catenates Pd-catalyz...
This review summarizes recent applications of copper or copper-based compounds as a nonprecious metal catalyst in N-nucleophiles-based dehalogenation (DH) reactions of halogenated aromatic compounds (Ar-Xs). Cu-catalyzed DH enables the production of...
Various substituted bis-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl2 in THF at −5 °C within 2 h. These bis-(aryl)manganes...
An efficient K3PO4-mediated synthesis of unsymmetrical diaryl ethers using the ionic liquid [Bmim]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) as solvent has been developed. The procedure involves consecutive deprotection of aryl methane-sulfo...
Nitriles are valuable compounds because they have widespread applications in organic chemistry. This report details the nickel-catalyzed reductive cyanation of aryl halides and epoxides with cyanogen bromide for the synthesis of nitriles. This robust...
A range of novel 4-amino-6-arylpyrimidines has been prepared under mild conditions by an electrochemical reductive cross-coupling between 4-amino-6-chloro-pyrimidines and functionalized aryl halides. The process, which employs a sacrificial iron anod...
Significant process intensification of the amination reactions of aryl halides and esters has been demonstrated using continuous flow processing. Using this technology traditionally difficult amination reactions have been performed safely at elevated...
In this article, we present a comprehensive computational investigation into the reaction mechanism of N-arylation of substituted aryl halides through Ullmann-type coupling reactions. Our computational findings, obtained through DFT ωB97X-D/6-3...
A copper-catalyzed direct sulfoxidation reaction by C(sp3)–H bond activation has been developed. Starting from sample aromatic methyl thioethers with aryl halides, versatile biologically-active arylbenzylsulfoxide derivatives were efficiently s...
A heterogeneous catalyst, nanosized MCM-41-Pd, was used to catalyze the Sonogashira coupling of aryl and heteroaryl halides with terminal alkynes in the presence of CuI and triphenylphosphine. The coupling products were obtained in high yields using...
In the last decades, numerous approaches have been explored for the cross-coupling of biaryl building blocks depending on the presence of boron sources. In fact, these changes have been catalyzed by transition metal complexes. This review focuses on...
We have successfully developed a novel cathodic cross-coupling reaction of aryl halides with arenes. Utilization of the cathodic single electron transfer (SET) mechanism for activation of aryl halides enables the cross-coupling reaction to proceed wi...
The dianion of 2,3’-biquinolyl with aryl- and hetaryl halides forms the products of arylation to 4’-position, which on treatment with alkyl halides or water yield 1’-alkyl-1’,4’dihydro-2,3’-biquinolyls or 4’-aryl-1’,4’-dihydro-2,3’-biquinolyls respec...
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...
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...
This paper describes the synthesis and catalytic testing of a palladium complex with a 5-membered chelating [N,O] ligand, derived from the condensation of 2,6-diisopropylphenyl aniline and maple lactone. This catalyst was active towards the Suzuki-Mi...
Palladium-catalyzed carbonylation reactions of ortho-phenylene dihalides were studied using aminoethanols as heterobifunctional N,O-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine and hydro...
A water-soluble PdCl2(NH3)2/cationic 2,2′-bipyridyl system was found to be a highly efficient catalyst for Stille coupling of aryl iodides and bromides with organostannanes. The coupling reaction was conducted at 110 °C in water, under aerobic condit...
In this study, we developed a palladium-catalyzed decarbonylative nucleophilic halogenation reaction using inexpensive and readily available acid anhydrides as substrates. This approach effectively circumvents the instability of acyl chlorides and th...
The comparison of the possibilities of Pd- and Cu-catalyzed amination reactions using fluorine-containing aryl bromides and iodides with oxadiamines to produce their N,N′-diaryl derivatives was carried out. The dependence of the reactivity of t...
A synthetic method for the preparation of 6-aryl-1,4-dimethyl-9H-carbazoles involving a palladium catalyzed coupling reaction of 1,4-dimethyl-9H-carbazole-6-boronic acids and (hetero)aryl halides is described.
Two polymer catalysts (Pd-OCMCS and Ni-OCMCS) with good reusability were synthesized by coordinating Pd and Ni onto O-carboxymethyl chitosan (OCMCS). The chemical structure and thermal stability of prepared catalysts were determined by Fourier transf...
(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...
(E)-1-aryl-2,4-bis(trimethylsilyl)but-1-en-3-ynes readily undergo protodesilylation and subsequent aerobic, copper-free Sonogashira cross-coupling with aryl halides to form (E)-1,4-diaryl-2-(trimethylsilyl)but-1-en-3-ynes. The proposed one-pot, two-s...
A tridentate bis-NHC Pd complex, based on caffeine, was studied for its catalytic activity. This complex displayed a high catalytic activity in the Suzuki–Miyaura and Mizoroki–Heck cross-coupling reactions of aryl halides. The Sonogashira...
A reaction of aromatic halides bearing electron-withdrawing groups with tertiary amines in the presence of an iridium catalyst under blue light irradiation is described. Products of the aromatic substitution of the halide by the dialkylamino fragment...
In the last few decades, organotin hydrides have proven their potential as building blocks for a great variety of organometallic compounds. In this context, organotin hydrides with sterically shielding aryl substituents have attracted special interes...
Methyl 4-(1,3a,6a-triazapentalen-3-yl)benzoate (TAP1) shows interesting properties as a small molecule fluorophore. In the search for post-functionalization methods, palladium-catalyzed arylation reactions were demonstrated. Direct CH arylation react...
Palladium-catalyzed carbonylation reactions, in the presence of nucleophiles, serve as very potent tools for the conversion of aryl and alkenyl halides or halide equivalents to carboxylic acid derivatives or to other carbonyl compounds. There are a v...
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...
Thioethers are critical in the fields of pharmaceuticals and organic synthesis, but most of the methods for synthesis alkyl thioethers employ foul-smelling thiols as starting materials or generate them as by-products. Additionally, most thiols are ai...
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...
Modification of 5-aryl-4-trifluoroacetyltriazoles at the NH-moiety was investigated. Screening of the alkylation conditions revealed that using Na2CO3 as a base and DMF as a solvent of 2-substituted triazoles can be preferentially prepared in up to 8...
The regioselectivity of the model compound 4-methyl-1-thioxo-1,2,4,5-tetrahydro[1,2,4]triazolo[4,3-a]quinazolin-5-one (3) towards different electrophiles was studied. Compound 3 reacts with alkyl and aryl halides to give the corresponding S-substitut...
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...
The construction of a C-S bond is a powerful strategy for the synthesis of sulfur containing compounds including sulfides, sulfoxides, and sulfones. Recent methodological developments have revealed lots of novel protocols for C-S bond formation, prov...
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...
The reaction of [PdCl2(CH3CN)2] and bis-4,4′-(RfCH2OCH2)-2,2′-bpy (1a–d), where Rf = n-C11F23 (a), n-C10F21 (b), n-C9F19 (c) and n-C8F17 (d), respectively, in the presence of dichloromethane (CH2Cl2) resulted in the synthesis of Pd complex, [PdCl2[4,...
A facile and efficient method for synthesizing diarylphosphinates from alcohols and aryl halides, using stable, green, and readily available sodium hypophosphite as a phosphorus source, is disclosed herein for the first time. This method offers high-...
11 aryl–lone pair and three aryl–anion
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