C–C bond formation is one of the most important implements in synthetic organic chemistry. In pursuit of effective synthetic routes functioning under greener pathways to achieve direct C–C bond formation, we report N-iodosuccinimide (NIS)...
Plasmonic hybrid nanostructures have been investigated as attractive heterogeneous photocatalysts that can utilize sunlight to produce valuable chemicals. In particular, the efficient photoconversion of CO2 into a stable hydrocarbon with sunlight can...
Heterogeneous recyclable catalysts in Suzuki-Miyaura C-C coupling reactions are of great interest in green chemistry as reusable alternatives to homogeneous Pd complexes. Considering the interesting properties of fluorinated compounds for the pharmac...
The use of nanostructure materials as heterogeneous catalysts in the synthesis of organic compounds have been receiving more attention in the rapid developing area of nanotechnology. In this review, we mainly focused on our own work on the synthesis...
Molecular modeling techniques and density functional theory calculations were performed to study the mechanism of enzymatic radical C–C coupling catalyzed by benzylsuccinate synthase (BSS). BSS has been identified as a glycyl radical enzyme that cata...
The activation of C–H bonds through catalytic reactions using transition metals is an important challenge in organic chemistry in which the intermediates are related to those produced in the classical cross-coupling reactions. As part of our re...
Ni catalysis constitutes an active research arena with notable applications in diverse fields. By analogy with its parent element palladium, Ni catalysts provide an appealing entry to build molecular complexity via cross-coupling reactions. While Pd...
Two high-performance Cu catalysts were successfully developed by immobilization of Cu ions in the nanospaces of poly(propylene imine) (PPI) dendrimer and magadiite for the selective C–C coupling of 2,6-dimethylphenol (DMP) to 3,3',5,5'-tetramethyldip...
The direct hydrogenation of greenhouse gas CO2 to higher alcohols (C2+OH) provides a new route for the production of high-value chemicals. Due to the difficulty of C-C coupling, the formation of higher alcohols is more difficult compared to that of o...
Cross-coupling reactions furnishing carbon–carbon (C–C) bond is one of the most challenging tasks in organic syntheses. The early developed reaction protocols by Negishi, Heck, Kumada, Sonogashira, Stille, Suzuki, and Hiyama, utilizing pa...
A method for “P-ligand free”, Pd(OAc)2-catalyzed P–C coupling reactions under MW conditions was investigated in our group. In our latest work, this procedure was extended to dihalogenobenzenes. Copper-promoted reactions were studied...
Traditional cross-coupling reactions, like Mizoroki-Heck Reaction and Suzuki Reaction, have revolutionized organic chemistry and are widely applied in modern organic synthesis. With the rapid development of C–H activation and asymmetric catalysis in...
Type II fatty acid synthases are promising drug targets against major bacterial pathogens. Platensimycin (PTM) is a potent inhibitor against β-ketoacyl-[acyl carrier protein] synthase II (FabF) and β-ketoacyl-[acyl carrier protein] synthase...
A literature survey of the P–C coupling reactions of 1,4-and 1,2-bromo-iodobenzenes with diphenylphosphine oxide or diethyl phosphite under different conditions comprising Pd-, Ni-, or Cu-catalysis revealed that, depending on the experimental d...
The application of metal–organic frameworks (MOFs) has attracted increasing attention in organic synthesis. The modification of MOFs can efficiently tailor the structure and improve the property for meeting ongoing demand in various application...
Aromatic substitution reactions between 1,3-diaminobenzene and chloronitrobenzofurazan derivatives have never been reported so far. The aim of the current study was to synthesize novel electron-donor and -acceptor architectures of interest in applied...
In recent years, nickel has entered the stage for catalyzed C–C cross-coupling reactions, replacing expensive palladium, and in some cases enabling the use of new substrate classes. Polypyridine ligands have played an important role in this developme...
The synthesis and structure of palladium complexes of trisubstituted PTA derivatives, PTAR3, are described. Water-soluble phosphine ligands 1,3,5-triaza-7-phosphaadmantane (PTA), tris(aminomethyl)phosphine trihydrobromide, tri(aminomethyl) phosphine,...
The fundamentals of Pd-catalyzed Csp2−Csp2 Miyaura borylation, Suzuki cross-coupling, and Stille cross-coupling reactions for a variety of borylated precursors based on phenothiazine (PTZ), phenoxazine (POZ), carbazole (Cz), and quinoxaline (QX...
Fulfilling the direct inert C–H bond functionalization of raw materials that are earth-abundant and commercially available for the synthesis of diverse targeted organic compounds is very desirable and its implementation would mean a great reduction o...
PAMAM dendrimers of generations G2–G3 as well as a partially substituted derivative of generation G4 and a low-molecular-weight tricyclic ligand 4 were used to bind Pd(0) nanoparticles. The obtained adducts were tested as catalysts for C–C cross-coup...
Palladium (Pd) is a 4d transition metal with electronic configuration [Kr] 4d10 5s0, and it is one of the most widely studied metals in the periodic table due to its versatile catalytic role in organic synthesis. The choice of ligands that can coordi...
The ever-growing interest in the cross-coupling reaction and its applications has increased exponentially in the last decade, owing to its efficiency and effectiveness. Transition metal-mediated cross-couplings reactions, such as Suzuki–Miyaura...
Aryl sulfides play an important role in pharmaceuticals, biologically active molecules and polymeric materials. Herein, a general and efficient protocol for Pd@COF-TB (a kind of Pd nanocatalyst supported by a covalent organic framework)/DIPEA-catalyz...
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...
Using biomass-derived solvents in various organic reactions is challenging for the fine chemicals industry. We herein report a Pd/C catalyzed Suzuki–Miyaura reaction in water extract of suaeda salsa (WES) without using external phosphine ligand...
Transition metal-catalyzed chemical transformation of organic electrophiles and organometallic reagents belong to the most important cross coupling reaction in organic synthesis. The biaryl ether division is not only popular in natural products and s...
Herein, we report a copper-catalyzed C-O cross-coupling of N-methoxy amides and arylboronic acids for the synthesis of aryl-N-methoxy arylimides. The fully selective O-arylation of the N-methoxy amides is found to be greatly prompted by the inexpensi...
The present study explores the potential of four NHC-palladium(II) complexes derived from (Z)- or (E)-styryl-N-alkylbenzimidazolium salts, namely trans-dichloro-[(Z)-1-styryl- 3-benzyl-benzimidazol-2-yliden]pyridine palladium(II) (6), trans-dichloro-...
The availability of water-soluble nanoparticles allows catalytic reactions to occur in highly desirable green environments. The catalytic activity and selectivity of water-soluble palladium nanoparticles capped with 6-(carboxylate)hexanethiolate (C6-...
Carbon-based molecules are of universal importance for a huge variety of chemical and biological processes. The complication of the structure of such molecules proceeds via the bonding of carbon atoms. An efficient mechanism for such reactions procee...
The reaction mechanism of Cu-catalyzed C-H hydroxylation/C-S coupling was studied using electrospray ionization high resolution mass spectrometry (ESI-HR MS) and density functional theory calculations (DFT). Notably, a series of CuI and CuIII complex...
The construction of carbon–carbon bonds by direct involvement of two unactivated carbon–hydrogen bonds, without any directing group, ensures a high atom economy of the entire process. Here, we describe a simple protocol for the Pd(II)/Cu(II)-promoted...
An oxidative 3-amination of indole derivatives using hypervalent iodine(III) and bissulfonimides, which proceeds via the formation of indolyl(aryl)iodonium imides, was developed. This reaction was followed by an indole-selective copper-catalyzed oxid...
Cross-coupling reactions have played a critical role enabling the rapid expansion of structure–activity relationships (SAR) during the drug discovery phase to identify a clinical candidate and facilitate subsequent drug development processes. T...
Donor-acceptor-donor (D-A-D) type molecules are of interest as components in organic light emitting diodes (OLEDs). In this communication, 4,7-bis(2,3,3a,8b-tetrahydrocyclopenta[b]indol-4(1H)-yl)-[1,2,5]thiadiazolo[3,4-c]pyridine was obtained by two...
The so far unattended version of the Hirao reaction involving the coupling of the less reactive chloroarenes with >P(O)H reagents, such as diarylphosphine oxides, diethyl phosphite, and ethyl phenyl-H-phosphinate, was investigated in detail using...
Our group described a green, “P-ligand-free”, Pd(OAc)2- or NiCl2-catalyzed synthesis under MW conditions. The reactivity of a few aryl derivatives in the Pd(OAc)2-catalyzed, “P-ligand-free” P–C coupling reactions under M...
Among transition metal nanoparticles, palladium nanoparticles (PdNPs) are recognized for their high catalytic activity in a wide range of organic transformations that are of academic and industrial importance. The increased interest in environmental...
The availability and application of direct, functional group-compatible C–H activation methods for late-stage modification of small-molecule bioactives and other valuable materials remains an ongoing challenge in organic synthesis. In the current stu...
The title compound—cis,exo-1,2,3,4,4a,13b-hexahydro-1,4-methano-5-isopropoxy-9H-tribenzo[b,f]azepine—was synthesized in 83% isolated yield by a palladium-catalyzed one-pot strategy from 1-iodo-2-isopropoxybenzene and ortho-bromoaniline. The azepine d...
The C-3 functionalization of 1H-indazole could produce a lot of highly valuable pharmaceutical precursors, which could be used for the treatment of cancer and many other inflammatory diseases. This work was focused on the C-3 functionalization of 1H-...
The six-membered N,S-heterocyclic 1,3-thiazines and their derivatives are widely acknowledged as pharmaceutical molecules with a wide range of biological activities. In this study, we developed a unique thiol-involved cascade reaction that enables th...
In the last years there has been an increasing interest in the search for protocols to obtain β-haloenol esters in an efficient and selective manner as they are versatile building blocks in synthetic organic chemistry. In this article, metal-cat...
Rhodium nanoclusters were uniformly dispersed on nano-scaled graphene platelets by a simple ‘mix and heat’ method without using any toxic reagents. Distilled water was used to obtain the homogenous dispersion of Rh-nanoclusters on graphen...
Mesitylene was used as a core in seven new tritopic nitrogen containing linkers. Three of the linkers, each containing three nitrile groups, were obtained through Suzuki, Sonogashira and Heck-type coupling reactions. Next, these were converted to tet...
The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustiv...
The synthetic potential of stereoselective, palladium-catalyzed hydro(het)arylation reactions of bi-, tri- and tetracyclic (hetero)alkenes in the presence of phospines and arsines as highly efficient ligands was studied. The mechanism of this reducti...
Herein, the preparation of neoglycoconjugates bearing mannose-6-phosphate analogues is described by: (a) synthesis of a cyclic sulfate precursor to access the carbohydrate head-group by nucleophilic displacement with an appropriate nucleophile; (b) i...
Water-soluble salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N’-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were...
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