54492-94-3

Upstream product

• 586-78-7 para-nitrophenyl bromide 
• 95-15-8 Benzo[b]thiophene 
• 636-98-6 p-nitrobenzene iodide 
• 63724-94-7 2-deuteriobenzothiophene 
• 2945-08-6 methyl (4-nitrophenyl)acetate 
• 6630-33-7 ortho-bromobenzaldehyde 
• 98437-23-1 benzo[b]thiophene-2-boronic acid 
• 100-00-5 4-chlorobenzonitrile 
• 62-53-3 aniline 
• 136-95-8 2-amino-benzthiazole 
• 2987-53-3 2-(Methylthio)aniline 
• 937-31-5 (4-Nitrophenyl)acetylene 

Relevant academic research and scientific papers

Synthesis of 2-Substituted Benzothio(seleno)phenes and Indoles via Ag-Catalyzed Cyclization/Demethylation of 2-Alkynylthio(seleno)anisoles and 2-Alkynyldimethylanilines

An Ag-catalyzed cyclization/demethylation of 2-alkynylthio(seleno)anisoles and 2-alkynyldimethylanilines is described and applied for the construction of valuable benzothio(seleno)phenes as well as indoles. Various 2-substituted benzothio(seleno)phenes and indoles were obtained in good to excellent yields under mild reaction conditions with low catalyst loading. An application of this new method is also exemplified with a concise synthesis of a bioactive molecule precursor. Furthermore, a conceivable reaction mechanism is proposed with supports from isotope-exchange experiments.

Infrared Irradiation-Assisted Solvent-Free Pd-Catalyzed (Hetero)aryl-aryl Coupling via C?H Bond Activation

The increasing attention towards environmentally friendly synthetic protocols has boosted studies directed to the development of green and sustainable methods for direct C?H bond arylation of (hetero)arenes. In this context, here the infrared (IR) irradia

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 derivative by catalysis of dihalogenated aromatics by copper

The invention discloses a method for synthesizing a benzothiophene derivative by catalysis of dihalogenated aromatics by copper. According to the invention, a catalyst cuprous iodide with a catalysisamount, a ligand 8-hydroxyquinoline, an auxiliary catalyst cesium carbonate and 1-bromine-2-iodobenzene or its derivative, sulfur powder, and phenylacetylene or its derivative are added in a flask andsubjected to a reaction in pure water at certain temperature, after a certain time, vacuum concentration is carried out, and a product is purified through column chromatography. The method has the advantages of novel raw material and simple operation, and can be used for efficiently preparing the benzothiophene derivative. Compared with the prior art, the method has the advantages of mild reaction condition, simple operation, high yield, safety, low cost, and environmental protection.

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.

Carbon-carbon bond formation catalyzed by PEPPSI Pd-NHC

Five new palladium complexes were efficiently synthesized from the reaction of benzimidazolium salts, potassium carbonate (K2CO3) and palladium chloride (PdCl2) in pyridine (for 3–5) or 3-chloropyridine (for 6 and 7). The synthesized complexes were characterized and tested in Suzuki-Miyaura cross-coupling reaction as catalysts. In the presence of catalysts 3–7, biaryl products were obtained in moderate yields when phenylboronic acid was used as boronic acid derivative. However, the coupling of thianaphthene-2-boronic acid with 1-chloro-4-nitrobenzene generated low yields although a longer period of time was used in comparison to the coupling of phenylboronic acid with aryl chlorides.

Microwave-assisted, ligand-free, direct C-H arylation of thiophenes in biomass-derived γ-valerolactone

The Pd-catalyzed C-H arylation of heterocycles with aryl halides is a straightforward and more environmentally-friendly route to the synthesis of well-defined, pi-conjugated polymers for challenging applications in electronic devices. Although this type of transformation is more atom efficient than cross-couplings, it still poses environmental issues in the form of reaction media and the use of phosphine ligands. A procedure for the C-H arylation of thiophenes, with a substantially improved environmental impact, and a promising application of this protocol to the synthesis of regioregular polythiophenes are reported in this work. γ-Valerolactone (GVL), a non-toxic biomass-derived solvent, has been used in this phosphine-free microwave-assisted process and replaces commonly used dipolar aprotic media. Activated aryl bromides gave arylthiophenes in good yields, while iodides were used and pivalic acid was added when electron-withdrawing groups were present. The reaction was also extended to C-H (hetero)arylation polycondensation and a high molecular weight poly(3-hexyl)thiophene was obtained, using low Pd loading, in high yields and good regioregularity in short reaction times. Computational studies have shed light on GVL's role as a ligand in the catalytic system.

Three-component 2-aryl substituted benzothiophene formation under transition-metal free conditions

A base-mediated 2-aryl substituted benzothiophene formation from 2-bromobenzene aldehydes, benzylic esters and elemental sulfur under transition-metal-free conditions is described. Various 2-aryl substituted benzothiophene were efficiently obtained under mild conditions.

N-Methylphthalimide-substituted Benzimidazolium salts and PEPPSI Pd-NHC complexes: Synthesis, characterization and catalytic activity in carbon-carbon bond-forming reactions

A series of novel benzimidazolium salts (1-4) and their pyridine enhanced precatalyst preparation stabilization and initiation (PEPPSI) themed palladium N-heterocyclic carbene complexes [PdCl2(NHC)(Py)] (5-8), where NHC = l-(N-methylphthalimide)-3-alkylbenzimidazolin-2-ylidene and Py = 3-chloropyridine, were synthesized and characterized by means of 1H and 13C{1H} NMR, UV-vis (for 5-8), ESI-FTICR-MS (for 2, 4, 6-8) and FTIR spectroscopic methods and elemental analysis. The synthesized compounds were tested in Suzuki-Miyaura cross-coupling (for 1-8) and arylation (for 5-8) reactions. As catalysts, they demonstrated a highly efficient route for the formation of asymmetric biaryl compounds even though they were used in very low loading. For example, all compounds displayed good catalytic activity for the C-C bond formation of 4-tert-butylphenyl-boronic acid with 4-chlorotoluene.

Palladacycles derived from arylphosphinamides for mild Suzuki-Miyaura cross-couplings

We present a type of palladacyclic complexes derived from arylphosphinamides which can be used as efficient and versatile precatalysts for mild Suzuki-Miyaura cross-coupling. With the presence of 1.0 mol% of palladacycles, a wide variety of aryl bromides and boronic acids could be coupled very efficiently at ambient temperature and under air atmosphere without the need of external supporting ligands. Moreover, the mild conditions also allow for smooth coupling of electron-deficient, i.e., the less stable aryl triflates. In addition to the highly catalytic activity, the palladacyclic complexes can be very easily prepared through a two-step procedure from the readily affordable diphenyl-phosphinic chloride and exhibit excellent stability toward air and moisture. Due to these prominent properties, the new palladacycles would find practical use in Suzuki-Miyaura couplings.