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Suzuki– Miyaura coupling
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Ebook "Organotrifluoroborate preparation, coupling and hydrolysis" reports on the reactivity of organotrifluoroborates, which are becoming increasingly important reagents in synthesis. The thesis is divided into three sections. The first section describes a method for preparing organotrifluoroborates. The second section reports on a mechanistic investigation into the main application of RBF3K reagents as coupling partners in Suzuki-Miyaura coupling, phenomena identified as arising from organotrifluoroborate hydrolysis and fluoride release.
235p
coduathanh1122
27-03-2024
3
1
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In the paper "Planar Geometry of 4-Substituted-2,2'-bipyridines Synthesized by Sonogashira and Suzuki Cross-Coupling Reactions", we report the synthesis, geometry and molecular arrangement in the crystals of two compounds, namely 4-(ferrocenylethynyl)-2,2'-bipyridine (I) and 4-ferrocenyl-2,2'-bipyridine (II) which were synthesized by the palladium catalyzed Sonogashira [5, 6] and Suzuki-Miyaura [7, 8] cross-coupling reactions.
6p
runordie3
27-06-2022
10
2
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The new complexes (1–3) were characterized by elemental analysis and spectroscopic methods and the molecular structure of 1a was determined by X-ray diffraction studies. These complexes were applied in the Suzuki–Miyaura cross-coupling reaction of phenylboronic acid with aryl halides in neat water. The activities of catalysts were monitored by gas chromatography–flame ionization detector and nuclear magnetic resonance.
10p
langthannam
29-12-2021
12
0
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Novel benzimidazolium salts having N-benzyl or N-(4-substitutedbenzyl) groups were synthesized and their microwave-promoted catalytic activity for the Suzuki–Miyaura cross-coupling reaction were determined using in situ formed palladium(0) nanoparticles (PdNPs) from a catalytic system consisting of Pd(OAc) 2 /K2CO3 in DMF/H2 O. PdNPs were characterized by X-ray diffraction (XRD) pattern and particle size of in situ generated PdNPs from the Pd(111) plane was determined to be of diameter 19.6 nm by the Debye–Scherrer equation.
13p
langthannam
29-12-2021
7
0
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This review is focused on new developments reported during the last 3 years concerning the catalytic performances of in situ formed or preformed NHC–Pd(II) complexes (NHC: N-heterocyclic carbene) for cross-coupling reactions such as Heck–Mizoraki (often shortened to the Heck reaction), Kumada, Negishi, Suzuki–Miyaura (often shortened to the Suzuki reaction), Sonogashira and Hiyama couplings, and the Buchwald–Hartwig aminations, which are extremely powerful in the formation of C–C and C–heteroatom bonds.
43p
langthannam
29-12-2021
14
0
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In this account the authors’ latest results in C–C coupling catalysis are reviewed. First, an efficient catalytic system for the Kumada–Tamao–Corriu coupling reaction based on NHC-phosphine (NHC = N-heterocyclic carbene) nickel complexes is presented. Then the use of palladium complexes of chiral ferrocenyl NHC-phosphines in the asymmetric Suzuki–Miyaura coupling reaction is reported. High catalytic activities and moderate enantioselectivities (ee up to 46%) were obtained.
13p
langthannam
29-12-2021
9
0
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Two N -heterocyclic carbene (NHC) palladium complexes of formula [PdBr2(NHC)(pyridine)] in which the carbenic ring is flanked by sterically crowded cavitand substituents were prepared from appropriate imidazolium salts bearing either two resorcinarene or a combination of resorcinarene and calixarene fragments. Both complexes displayed high stability and good activities in the cross-coupling of aryl bromides with phenyl boronic acid. One of the imidazolium salts was characterised by an X-ray diffraction study.
9p
langthannam
29-12-2021
6
0
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We have developed a simple synthetic methodology for bis-spirocycles and spiroindole derivatives starting with a commercially available 6-bromo-2-tetralone. Here, we have used Fischer indolization, ring-closing metathesis, and Suzuki–Miyaura cross-coupling as key steps to assemble a variety of spirocyclic frameworks. The methodology developed here is simple and it may be useful to prepare various spirocycles containing indole moiety.
9p
langthannam
29-12-2021
6
0
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A green and efficient protocol has been developed for the Pd(OAc)2-catalyzed ligand-free Suzuki–Miyaura reaction of N-methyliminodiacetic acid (MIDA) boronates in water. In the presence of Pd(OAc)2 as a catalyst and (i-Pr)2NH as a base, the cross-coupling reactions of aryl bromides with aryl MIDA boronates proceeded smoothly in water without any surfactant, and various functional groups were tolerated under the optimized conditions.
8p
langthannam
29-12-2021
5
0
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Pd/C-PPh3–CuI catalyzed Sonogashira cross-coupling of the 2-aryl-6,8-dibromo-2,3-dihydroquinolin-4(1H)-ones with phenyl acetylene or 3-butyn-1-ol afforded the corresponding 8-alkynylated quinolin-4(1H)-one derivatives, exclusively. Double carbo-substitution to afford the 6,8-dialkynyl derivatives was observed when PdCl2(PPh3)2 was used as Pd(0) source.
16p
langthannam
29-12-2021
2
0
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Addressed herein is the catalysis of monodisperse palladium nanoparticles (NPs) supported on chemically derived graphene (CDG) for the Suzuki–Miyaura cross-coupling of phenylboronic acid and various aryl halides. Monodisperse Pd NPs were synthesized by the solution phase reduction of palladium(II) acetylacetonate with morpholine borane complex in oleylamine and deposited on CDG via the liquid phase self-assembly method. Colloidal Pd NPs and CDG-Pd catalyst were characterized by TEM, XRD, SEM, and ICP-MS analyses.
10p
langthannam
29-12-2021
11
0
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The novel benzimidazole salts (1–5), Pd(OAc)2, Cs2CO3, PEG, and Cu nanoparticles catalyzed, in high yield, the Sonogashira coupling reaction promoted by microwave irradiation in 10 min. The same benzimidazole salts (1–5), Pd(OAc)2, Cs2CO3, and TBAB catalyzed, in moderate or low yield, the Buchwald–Hartwig reaction assisted by microwave irradiation in 60 min. The efficiency of the catalyst system in these four reactions was discussed as well as the electron-releasing and withdrawing substituent effects on the benzimidazole ligands.
26p
langthannam
29-12-2021
9
0
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Two new diaminophosphine ligands, N ,N ’-bis(dicyclohexylphosphino)-2-(aminomethyl)aniline (1) and N ,N ’-bis(diisopropylphosphino)-2-(aminomethyl)aniline (2) were synthesized by the reaction of 2-(aminomethyl)aniline with two equivalents of Cy2PCl or (iPr)2PCl, respectively. Organophosphorus ligands have been extensively used in organometallic and inorganic chemistry, 1 and are mainly important in homogeneous catalysis.
11p
langthannam
29-12-2021
9
0
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The incorporation of N -coordinated benzimidazole complexes of palladium gave high catalytic activity in the Suzuki–Miyaura coupling of aryl halides substrates. After determining the best active catalyst as 5A1, bearing the mesityl substituent on the benzimidazole ring with the Pd(II) ion, optimization studies were carried out via changing the substrate, base, time, atmosphere, and the effect of water. The DMF:H2O (4/1) and Cs2CO3 as base were found to be critical for the efficiency of the reaction yield (100%).
11p
langthannam
29-12-2021
12
0
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Resorcinarene-mono-benzimidazolium salts as NHC ligands for Suzuki–Miyaura cross-couplings catalysts
Two mono-benzimidazolium salts of resorcinarene have been prepared and used as ligands in Suzuki–Miyaura cross-coupling reactions. They have been fully characterized by 1H and 13C NMR, MALDI, and FT-IR spectroscopic methods, and their structures were confirmed by X-ray diffraction analysis. These two new resorcinarene-based monobenzimidazolium salts showed good catalytic activity for coupling reactions in DMF. The highest conversion was achieved for arylation of 4-bromotoluene using the resorcinarenyl mono-dimethylbenzimidazolium salt.
11p
langthannam
29-12-2021
9
0
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Many benzimidazole salts bearing a 3-phenylpropyl substituent (1a–1h) were synthesized and their structures were identified by 1H NMR, 13C NMR, and IR spectroscopic methods and elemental analysis. These N-heterocyclic carbene (NHC) precursors were used as a part of a catalytic system including Pd(OAc) 2 and the base in the Suzuki– Miyaura cross-coupling reaction under microwave irradiation. They were also used as catalysts in the cyclotrimerization of phenyl isocyanate to yield 1,3,5-triphenyl-1,3,5-triazinane-2,4,6-trione.
31p
tudichquannguyet
29-11-2021
3
1
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The synthesis of 3 benzimidazole-based ionic Pd(II)-NHC complexes (NHC:N -heterocyclic carbene) is presented. The structures of the complexes are as follows: [NHC-PdBr3]−[NHC]+. The ionic palladium(II)-NHC complexes were synthesized in high yields and were fully characterized by nuclear magnetic resonance spectroscopy, X-ray diffraction, LC-MS/MS, and elemental analysis. These complexes have been identified as active catalysts in Suzuki–Miyaura reactions in a solution of 2-propanol and water at room temperature for different aryl bromides.
20p
tudichquannguyet
29-11-2021
10
1
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Suzuki C–C cross-coupling of aryl halides with aryl boronic acids using new phosphene-free palladium complexes as precatalysts was investigated. A pyridine-based Pd(II)-complex was used in open air under thermal as well as micro‑ wave irradiation conditions using water as an eco-friendly green solvent.
9p
vijiraiya2711
27-05-2020
10
1
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A facile and efficient palladium-catalyzed borylation of aryl (pseudo)halides at room temperature has been developed. Arylboronic esters were expeditiously assembled in good yields and with a broad substrate scope and good functional group compatibility.
8p
vijiraiya2711
27-05-2020
7
1
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The crystal structures of 2,5-di(ethoxyphenyl)-3,6-dibromothieno[3,2-b]thiophene (I) and 2,5-di(ethoxyphenyl)- 3,6-diphenylthieno[3,2-b]thiophene (II) have been studied in order to evaluate the planarity of these molecules. The aromatic systems introduced to the thieno[3,2-b]thiophene core structure show a degree of rotation from 30.94 to 66.56 . The crystal packing of (I) are characterized by π π stacking, while in (II), C-H and C-H O interactions are observed.
6p
lamtan3547
04-11-2018
15
0
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