The application of the Suzuki-Miyaura reaction in the synthesis of flavonoids, an important class of natural products, is reviewed. This reaction has not only been employed to provide access to flavonoid nuclei, but has also been applied to the synth...
New diarylquinazolines displaying pharmaceutical potential were synthesized in high yields from 4,7-dichloro-2-(2-methylprop-1-enyl)-6-nitroquinazoline by using microwave-promoted regioselective Suzuki-Miyaura cross-coupling reactions.
In this work, a Pd(II)-C,N-cyclometalated complex was grafted to polysiloxanes via azide–alkyne cycloaddition. The obtained polymer–metal complex (Pd-PDMS) acts as a catalyst in the Suzuki–Miyaura reaction. Pd-PDMS was drop-casted o...
The continuous flow Suzuki-Miyaura reaction between various haloarenes and arylboronic acids was successfully achieved within only ca. 20 s during the single-pass through a cartridge filled with palladium on carbon (Pd/C). No palladium leaching was...
In this study, a kilogram-scale synthesis of a potent TRPV1 antagonist, 1, is described. To synthesize bipyridinyl benzimidazole derivative 1, we have developed a scalable Suzuki–Miyaura reaction capable of providing a key intermediate, 6&prime...
Herein, we report the use of the Suzuki–Miyaura cross-coupling reaction for the preparation of a library of synthetic derivatives of flavonoids for biological activity assays. We have investigated the reactivity of halogenated flavonoids with a...
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...
An efficient arylation of SEM-protected pyrroles by the Suzuki–Miyaura coupling reaction has been developed. The reaction can be carried out under mild conditions to provide aryl-substituted pyrroles in moderate to excellent yields. The scope a...
Biomimetic N-acetylcysteamine thioesters are essential for the study of polyketide synthases, non-ribosomal peptide synthetases and fatty acid synthases. The chemistry for their preparation is, however, limited by their specific functionalization and...
We reveal the Suzuki–Miyaura reaction catalyzed by a Pd–Co nanocatalyst supported by Mg–Fe–CHT (calcined hydrotalcites). A variety of boronic acids and aryl halides were transformed into functionalized biphenyls in excellent y...
Nanoformulated calix[8]arenes functionalized with N-heterocyclic carbene (NHC)-palladium complexes were found to be efficient nano-reactors for Suzuki-Miyaura cross-coupling reactions of water soluble iodo- and bromoaryl compounds with cyclic triol a...
Pd(II) and Pt(II) composites with activated carbon (AC), graphene oxide, and multiwalled carbon nanotubes were prepared by ball milling and used as catalysts for the Suzuki-Miyaura reaction, under several energy inputs (mechanical grinding, conventio...
In the present work, a new heterogeneous catalyst Pd-NHC@Eu-BCI was synthesized by introducing N-heterocyclic carbene–palladium active sites into a 2D coordination polymer [Eu(BCI)(NO3)2H2O]n (Eu-BCI) based on a 1,3-bis(carboxymethyl)imidazoliu...
In the experimental work leading to this contribution, the parameters of the ultrasound treatment (temperature, output power, emission periodicity) were varied to learn about the effects of the sonication on the crystallization of Ni nanoparticles du...
In this study, we developed a novel catalysts consisting of periodic mesoporous organosilica functionalized with bipyridinium ionic liquid supported palladium. The physiochemical properties of the hybrid catalyst were investigated using Fourier trans...
Eco-compatible activation methods in Suzuki–Miyaura cross-coupling reactions offer challenging opportunities for the design of clean and efficient synthetic processes. The main enabling technologies described in the literature are microwaves, ultraso...
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 branched structures of dendronized polymers can provide good steric stabilization for metal nanoparticle catalysts. In this work, an amphiphilic dendronized copolymer containing hydrophilic branched triethylene glycol moieties and hydrophobic bra...
Palladium nanoparticles (Pd NPs) synthesized by the metal vapor synthesis technique were supported on poly(4-vinylpyridine) 2% cross-linked with divinylbenzene (Pd/PVPy). Transmission electron microscopy revealed the presence of small metal nanoparti...
Among the main reactions in organic chemistry, the Suzuki–Miyaura cross-coupling reaction catalyzed by a homogeneous or heterogeneous palladium complex is undoubtedly the most important [...]
A number of novel benzimidazolium salts having aryl substituents such as N-phenyl, 4-chlorophenyl and various alkyl substituents were synthesized. Their microwave-assisted catalytic activities were evaluated in Heck-Mizoroki and Suzuki-Miyaura cros...
In order to examine the effect of oriented (static) electric fields (OEF) on the kinetics of some representative Suzuki–Miyaura and metal-cluster mediated reactions at ambient temperatures, density functional theory-based calculations are repor...
A number of novel benzimidazole derivatives 1–4 were synthesized and the catalytic activity of these compounds in a catalytic system consisting of a benzimidazolium salt/Pd(OAc)2/K2CO3 were investigated in the Suzuki-Miyaura and Ullmann type homocoup...
The first access to N-1, N-4 disubstituted pyrrolo[2,3-d][1,2,3]triazoles is reported. The series were generated using a “one-pot” MCR, leading to a single regioisomer of the attempted heteroaromatic skeleton in good yields. Next, the fun...
Introduction: N-heterocyclic carbenes (NHCs) are considered important preferred auxiliary ligands for transition metals due to their strong σ-donor and weak π-acceptor properties and ease of structural modification in catalyst design. The fu...
The Suzuki-Miyaura reaction (SMR), involving the coupling of an organoboron reagent and an organic halide or pseudo-halide in the presence of a palladium or nickel catalyst and a base, has arguably become one of most utilized tools for the constructi...
A critical review of conclusions about the putative heterogeneous mechanism in the Suzuki-Miyaura coupling by supported Pd solids is reported. In the first section, the turnover frequencies (TOF) of 20 well-established homogeneous catalysts are shown...
Unlike the wide number of natural biflavonoids, natural bichalcones are a rare and even less studied class. Nevertheless, some of them have proved their interest in the fight against cancer through their cytotoxic activity against human tumor cell li...
A systematic synthetic study was performed to explain the usual trend in selectivity towards multi-coupling, over mono-coupling, in Suzuki–Miyaura reactions. This preference was observed under different reaction conditions: for various halobenz...
Plasmonic nanostructures can be employed for performing photocatalytic reactions with visible-light illumination involving two different possible mechanisms, namely, the near-field enhancement and/or direct hot-electron transfer to the conduction ban...
Palladium-catalyzed cross-coupling reactions are nowadays essential in organic synthesis for the construction of C–C, C–N, C–O, and other C-heteroatom bonds. The 2010 Nobel Prize in Chemistry to Richard F. Heck, Ei-ichi Negishi, and...
The synthesis of new vicinal diamines based on aziridine and azetidine cores as well as the comparison of their catalytic activities as ligand in the Suzuki-Miyaura coupling reaction are described in this communication. The synthesis of three- and fo...
The cyclin-dependent kinase inhibitor, CAN508, was protected with di-tert-butyl dicarbonate to access the amino-benzoylated pyrazoles. The bromo derivatives were further arylated by Suzuki-Miyaura coupling using the XPhos Pd G2 pre-catalyst. The coup...
The reactivity of the 7-chloro-8-iodo- and 8-chloro-7-iodoimidazo[1,2-a]pyridines 1a–e diversely substituted on the 2 position, towards Suzuki-Miyaura, Sonogashira, and Buchwald-Hartwig cross-coupling reactions as well as cyanation was evaluated. Var...
The Suzuki–Miyaura coupling reaction is one of the most widely utilized C–C bond forming methods to create (hetero)biaryl scaffolds. The continuous-flow reaction using heterogeneous catalyst-packed cartridges is a practical and efficient...
Covalent organic framework (COF)-supported palladium catalysts have garnered enormous attention for cross-coupling reactions. However, the limited linkage types in COF hosts and their suboptimal catalytic performance have hindered their widespread im...
Palladacycles are highly efficient precatalysts in cross-coupling reactions whose immobilization on carbonaceous materials has been hardly studied. Herein, we report a detailed study on the synthesis and characterization of new oxime palladacycle-gra...
Following our previous results on an environmentally benign one-pot Sonogashira-cyclization protocol to obtain substituted furopyrimidine nucleosides under aqueous conditions, we investigate herein the Suzuki-Miyaura cross-coupling reactions of aryl...
In this communication, we present the results obtained using a family of cyclometallated palladium compounds as catalysts for the Suzuki–Miyaura cross-coupling reaction between an aryl halide and phenylboronic acid. We have studied the structur...
A novel heterogeneous transition-metal catalyst comprising a polymer-supported terpyridine palladium(II) complex was prepared and found to promote the Suzuki-Miyaura, Mizoroki-Heck, Sonogashira, and Tsuji-Trost, reactions in water under aerobic condi...
Furyl and thienyl moieties were introduced into a purine structure to elevate its fluorescence properties, while a trityl group was used to increase the amorphous properties of the purine compounds. The title compounds were prepared by a sequence inv...
A ligand-free approach for the Suzuki-Miyaura cross coupling reaction using Natural Deep Eutectic Solvents (NaDES) towards coumarin analogs is described. A model reaction between the synthetically prepared 3-(4-acetyloxy-phenyl)-6-bromo-4-methyl-coum...
Intramolecular transfer of t-Bu3P-ligated Pd catalyst on a carbon–carbon triple bond (C≡C) and nitrogen–nitrogen double bond (N=N) was investigated and compared with the case of a carbon–carbon double bond (C=C), which is resistant to intramolecular...
In this study, mesoporous and nonporous silica-supported Pd complexes were synthesized and characterized. Variable-temperature XAFS measurements and a curve-fitting analysis showed a slightly larger contribution of σ2static when the Pd complexes were...
An efficient, versatile, and one-pot method for the preparation of novel fluorinated thiazolo- and oxazolo[3,2-a]pyrimidin-7-ones is described from 2-aminothiazoles or 2-amino-oxazoles and fluorinated alkynoates. This transformation, performed under...
A new series of xylyl-linked bis-benzimidazolium salts were efficiently prepared using a simple preparation method from bis-benzimidazolium precursors featuring highly tunable linkers and wingtips. A highly efficient Suzuki–Miyaura cross-coupling rea...
The present study demonstrates the fabrication of a conjugated porous polymer (CPP-P2) through a Pd-catalyzed Suzuki–Miyaura poly-condensation reaction. 13C cross-polarization solid-state NMR and Fourier transform infrared (FTIR) spectroscopy w...
Direct 2(5H)-furanone annulation produces promising cross-coupling partners incorporating m- or p-bromo- and p-tosyloxyphenyl groups into the 5-position of a notable 2(5H)-furanone pharmacore. The present one-pot annulation method involves two distin...
The catalyst activities of various heterogeneous palladium catalysts supported by anatase-, rutile- and brookite-type titanium oxide for ligand-free Suzuki–Miyaura cross-coupling reactions of aryl chlorides were evaluated. Palladium acetate [Pd...
The potentialities of mechanochemistry trough extrusion have been investigated for the design of nanosized catalysts and their use in C-C bond-forming reactions. The mechanochemical approach proved successful for the synthesis of supported palladium...
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