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Room-temperature hydrodehalogenation of halogenated heteropentalenes with one or two heteroatoms

The pair NaBH4-TMEDA as a hydride source and catalytic PdCl 2(dppf) in THF prove to be an efficient system for the hydrodehalogenation of bromo(chloro)-heteropentalenes with one or two heteroatoms, while Pd(OAc)2/PPh3 is able to reduce reactive haloheteropentalenes, and PdCl2(tbpf) allows the removal of the 2-chlorine from a thiophene ring. The reaction conditions tolerate various functional groups, allowing highly chemoselective reactions in the presence of halide, ester, alkyne, alkene, and nitrile substituents and also showing good efficiency in the regioselective hydrodehalogenation of a variety of polyhalogenated substrates.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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5394-13-8, Name is 2-Bromobenzo[b]thiophene, belongs to benzothiophene compound, is a common compound. 5394-13-8In an article, authors is Atwater, Bruce, once mentioned the new application about 5394-13-8.

The Selective Cross-Coupling of Secondary Alkyl Zinc Reagents to Five-Membered-Ring Heterocycles Using Pd-PEPPSI-IHeptCl

The ability to cross-couple secondary alkyl centers is fraught with a number of problems, including difficult reductive elimination, which often leads to beta-hydride elimination. Whereas catalysts have been reported that provide decent selectivity for the expected (non-rearranged) cross-coupled product with aryl or heteroaryl oxidative-addition partners, none have shown reliable selectivity with five-membered-ring heterocycles. In this report, a new, rationally designed catalyst, Pd-PEPPSI-IHeptCl, is demonstrated to be effective in selective cross-coupling reactions with secondary alkyl reagents across an impressive variety of furans, thiophenes, and benzo-fused derivatives (e.g., indoles, benzofurans), in most instances producing clean products with minimal, if any, migratory insertion for the first time. A wide variety of five-membered-ring heterocycles were successfully cross-coupled to secondary alkyl zinc reagents with the new precatalyst Pd-PEPPSI-IHeptCl, which features a bulky N-heterocyclic carbene ligand. This catalyst suppresses migratory-insertion (rearrangement) pathways, and the desired products are thus formed with high selectivity.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Lithium-Free Synthesis of Sodium 2,2,6,6-Tetramethylpiperidide and Its Synthetic Applications

Lithium-free synthetic methods for sodium 2,2,6,6-tetramethylpiperide (NaTMP) have been developed using sodium dispersion as a sole sodium source. The prepared NaTMP was used as a Br¡ãnsted base, that exhibited some differences in reactivities from LiTMP. (Figure presented.).

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One of the major reasons for studying chemical kinetics is to use measurements of the macroscopic properties of a system, 5394-13-8, such as the rate of change in the concentration of reactants or products with time.In a article, authors is Montserrat Martinez, mentioned the application of 5394-13-8, Name is 2-Bromobenzo[b]thiophene, molecular formula is C8H5BrS

Synthesis of functionalized thiophenes and oligothiophenes by selective and iterative cross-coupling reactions using indium organometallics

The synthesis of unsymmetrical 2,5-disubstituted thiophenes by selective and sequential palladium-catalyzed cross-coupling reactions of indium organometallics with 2,5-dibromothiophene is reported. Following an iterative coupling sequence, alpha-oligothiophenes were synthesized in good yields and with high atom economy.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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Heterogeneous palladium catalyst constructed with cross-linked hyperbranched poly(phenylacetylene) as polymer support: A reusable highly active ppm-level catalyst for multiple cross-coupling reactions

We demonstrate in this work a unique strategy for the synthesis of heterogeneous Pd catalysts with the use of a hyperbranched poly(phenylacetylene) containing pendant alkyne groups as the cross-linkable polymer substrate. It utilizes the dual functions of Pd-based catalysts in catalyzing both alkyne polymerization/oligomerization and coupling reactions. In the synthesis, a homogeneous Pd(II) catalyst catalyzes the cross-linking of the hyperbranched polymer and simultaneously encapsulates itself into the crosslinked polymer matrix, rendering the heterogeneous catalyst at high yield and high percentage of Pd encapsulation. Three homogeneous catalysts having different ligands (triphenylphosphine, a diphosphine ligand, and a diimine ligand) have been examined for the cross-linking encapsulation and the resulting heterogeneous catalysts have been evaluated for their catalytic performance in coupling reactions. Among the various heterogeneous catalysts obtained, a triphenylphosphine-ligated catalyst, HBPPA-Pd-2, appears to be the optimum one. It shows high activity in catalyzing the Suzuki-Miyaura reactions, the Mizoroki-Heck reactions, and the allylic arylation reactions under air with the Pd loading at as low as mol ppm or even mol ppb levels relative to the reactants. Meanwhile, it facilitates the Suzuki-Miyaura reactions of challenging less reactive aryl chlorides/heteroaryl bromides and the Mizoroki-Heck reactions of aryl bromides as reactants. In addition, it behaves truly as a heterogeneous catalyst with high reusability and low catalyst leaching during the reactions.

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Benzothiophene – Wikipedia,
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5394-13-8, Chemistry can be defined as the study of matter and the changes it undergoes. You¡¯ll sometimes hear it called the central science because it is the connection between physics and all the other sciences, starting with biology.5394-13-8, Name is 2-Bromobenzo[b]thiophene, molecular formula is C8H5BrS, introducing its new discovery.

Nickel-Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry

Transition-metal-catalyzed coupling reactions are useful tools for synthesizing aryl sulfur compounds. However, conventional transition-metal-catalyzed thiolation of aryl bromides and chlorides typically requires the use of strong base under elevated reaction temperature. Herein, we report the first examples of nickel-catalyzed electrochemical thiolation of aryl bromides and chlorides in the absence of an external base at room temperature using undivided electrochemical cells.

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Palladium-Catalyzed Germylation of Aryl Bromides and Aryl Triflates Using Hexamethyldigermane

Palladium-catalyzed germylation of aryl bromides and aryl triflates using commercially available hexamethyldigermane is described. Optimized reaction conditions afforded various functionalized aryltrimethylgermanes, including drug-like molecules, in moderate to good yields, demonstrating the versatility of the presented protocols.

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Transition-Metal-Free Cross-Coupling of Benzothiophenes and Styrenes in a Stereoselective Synthesis of Substituted (E,Z)-1,3-Dienes

A transition metal-free one-pot stereoselective approach to substituted (E,Z)-1,3-dienes was developed by using an interrupted Pummerer reaction/ligand-coupling strategy. Readily available benzothiophene S-oxides, which can be conveniently prepared by oxidation of the parent benzothiophenes, undergo Pummerer coupling with styrenes. Reaction of the resultant sulfonium salts with alkyllithium/magnesium reagents generates underexploited hypervalent sulfurane intermediates that undergo selective ligand coupling, resulting in dismantling of the benzothiophene motif and the formation of decorated (E,Z)-1,3-dienes.

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Enantioselective Synthesis of Carbo- and Heterocycles through a CuH-Catalyzed Hydroalkylation Approach

The enantioselective, intramolecular hydroalkylation of halide-tethered styrenes has been achieved through a copper hydride-catalyzed process. This approach allowed for the synthesis of enantioenriched cyclobutanes, cyclopentanes, indanes, and six-membered N- and O-heterocycles. This protocol was applied to the synthesis of the commercial serotonin reuptake inhibitor (?)-paroxetine.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem

 

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5394-13-8, Catalysts are substances that increase the reaction rate of a chemical reaction without being consumed in the process. 5394-13-8, Name is 2-Bromobenzo[b]thiophene, molecular formula is C8H5BrS. In a Article, authors is Neumann, Karoline T.£¬once mentioned of 5394-13-8

Palladium-catalyzed carbonylative sonogashira coupling of aryl bromides using near stoichiometric carbon monoxide

A general procedure for the palladium-catalyzed carbonylative Sonogashira coupling of aryl bromides is reported, using near stoichiometric amounts of carbon monoxide. The method allows a broad substrate scope in moderate to excellent yields. The formed alkynone motive serves as a platform for synthesis of various heterocyclic structures, including pyrimidines. Furthermore, the presented strategy allows effective 13C labeling.

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Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem