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• 95-46-5 2-methylphenyl bromide 
• 120878-74-2 α,α-diphenyl-benzo[b]thien-2-ylmethanol 
• 98437-23-1 benzo[b]thiophene-2-boronic acid 
• 1191415-24-3 2-(2,2-dibromovinyl)benzenethiol 
• 16419-60-6 2-Methylphenylboronic acid 
• 1314235-27-2 1-bromo-2-(o-tolylethynyl)benzene 
• 615-37-2 ortho-methylphenyl iodide 
• 766-46-1 2-bromo-1-ethynylbenzene 
• 95-15-8 Benzo[b]thiophene 
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• 50684-47-4 2-methyl-thiobenzoic acid 
• 62680-65-3 (2-iodobenzyl)triphenylphosphonium bromide 
• 17763-67-6 Phenyl triflate 
• 1207-95-0 2-phenylbenzo[b]thiophene 

Relevant academic research and scientific papers

Nickel-catalyzed and Li-mediated regiospecific C-H arylation of benzothiophenes

A nickel-based catalytic system for the regiospecific C2-H arylation of benzothiophene has been established. NiCl2(bpy) is used as a catalyst in combination with LiHMDS as a base in dioxane. The catalytic system is applicable to a variety of functionalized benzothiophenes, as well as other heteroarenes including thiophene, benzodithiophene, benzofuran and selenophene in combination with iodo aryl electrophiles. The role of LiHMDS as a uniquely potent base and a postulated mechanism are discussed. The applicability of this system is finally demonstrated for the synthesis of an intermediate of an active pharmaceutical ingredient.

C-H Arylation of Thiophenes with Aryl Bromides by a Parts-per-Million Loading of a Palladium NNC-Pincer Complex

A palladium NNC-pincer complex efficiently catalyzed the direct arylation of thiophene derivatives with extremely low palladium loadings of the order of parts per million. Thus, the reaction of various thiophenes with aryl bromides in the presence of 25-100 mol ppm of chlorido[(2-phenyl-κ- C 2)-9-phenyl-1,10-phenanthroline-κ 2- N, N ′]palladium(II) NNC-pincer complex, K 2CO 3, and pivalic acid in N, N -dimethyl acetamide afforded the corresponding 2- or 5-arylated thiophenes in good to excellent yields. A combination of the present C-H arylation and Hiyama coupling with the same NNC-pincer complex provides an efficient synthesis of unsymmetrical 2,5-thiophenes with catalyst loadings at mol ppm levels.

Ag(I)-C-H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[ b]thiophenes

The first example of near-room-temperature α-arylation of benzo[b]thiophenes is reported. The discovery rests on the observation of a switch in α-/β-regioselectivity at different loadings of Pd2(dba)3·CHCl3 in the coupling between benzo[b]thiophene and 4-iodotoluene. We show that this unprecedented regioselectivity switch is driven by a Ag(I)-mediated C-H activation at the α-C-H position, which becomes the dominant mode of reactivity at low concentrations of Pd. Competition experiments, kinetic studies, KIE, and D/H scrambling experiments have been carried out supporting this mechanism.

Method for synthesizing benzothiophene derivatives from dihaloarene under microwave irradiation under catalysis of copper

The invention discloses a method for synthesizing benzothiophene derivatives from dihaloarene under microwave irradiation under the catalysis of copper. The method comprises the following steps: adding a catalytic amount of a catalyst copper chloride, a ligand 1,10-phenanthroline (1,10-Phen), a cocatalyst potassium hydroxide, 1-bromo-2-iodobenzene and its derivatives, KSCN (potassium thiocyanate),phenylacetylene and pure water, performing a reaction in a microwave reactor at a certain temperature under a certain power for a certain time, performing reduced pressure concentrating, and performing column chromatography purification on the obtained product. The method disclosed in the invention is a method having novel raw materials, being simple to operate and used for efficiently preparingthe benzothiophene derivatives. Compared with the prior art, the method has an obvious faster reaction speed than convectional heating, and has the advantages of mild reaction conditions, simplicity in operation, high yield, safety, low cost and environmental protection.

N-Heterocyclic carbene-Pd(II)-1-methylimidazole complex catalyzed C[sbnd]H bond arylation of (benzo)thiophenes with aryl chlorides

NHC-Pd(II)-Im complex showed efficient catalytic activity toward the direct C[sbnd]H bond arylation of (benzo)thiophenes with the challenging aryl chlorides. Under the suitable conditions, all reactions proceeded smoothly to give the desired C[sbnd]H bond

Arylation method of thiophene compounds

The invention provides an arylation method of thiophene compounds. The thiophene compounds are benzothiophene or thiophene, and the benzothiophene represented by formula (1) or thiophene represented by formula (2) and aryl chloride represented by formula

Palladium-Catalyzed Direct C2-Arylation of Benzo[ b ]thiophenes with Electron-Rich Aryl Halides: Facile Access to Thienoacene Derivatives

Direct coupling reaction of benzo[ b ]thiophene and electron-rich aryl bromides was achieved under Pd 2 (dba) 3 /SPhos catalysis in the presence of NaO t -Bu. The reaction system was applied for the installation of 2-(methylthio)phenyl group onto thiophene-fused polyaromatic molecules, demonstrating facile synthesis of precursors for thienoacene derivatives.

Iridium-Catalyzed Asymmetric Hydrogenation of Benzo[b]thiophene 1,1-Dioxides

An efficient iridium-catalyzed asymmetric hydrogenation of substituted benzothiophene 1,1-dioxides is described. The use of iridium complexes with chiral pyridyl phosphinite ligands provides access to highly enantiomerically enriched sulfones with substituents at the 2- and 3-position. Sulfones of this type are of interest as core structures of agrochemicals and pharmaceuticals. Moreover, they can be further reduced to chiral 2,3-dihydrobenzothiophenes.

A benzothiophene compound preparation method and its purification method

The invention discloses a preparation method for benzothiophene compounds. The preparation method comprises the following steps: 1-bromine(chlorine)-2-styrene benzene or derivatives thereof are used as a substrate; a vulcanizer is added into the substrate

Bulky α-diimine palladium complexes: Highly efficient for direct C-H bond arylation of heteroarenes under aerobic conditions

Through the strategy to enhance the bulkiness on both the backbone and the N-aryl moieties, we designed and synthesized a type of bulky α-diimine palladium complex (i.e., {[Ar-NC(R)-C(R)N-Ar]PdCl2, (Ar = 2-benzhydryl-4,6-dimethylphenyl)}, C1, R = H; C2, R = An; C3, R = Ph). The structures of these palladium complexes were well characterized, while C1 and C3 were further characterized by X-ray diffraction. The catalytic performances of the precatalysts were screened for direct C-H bond arylation of heteroarenes. The bidentate N,N-palladium complex C3 with both a backbone and N-aryl bulkiness was found to be a highly efficient precatalyst under aerobic conditions. With a low palladium loading of 0.5-0.1 mol%, a variety of heteroarenes with challenging bulky steric aryl bromides as well as heteroaryl bromides are all applicable for this cross-coupling reaction.