936734-94-0Relevant articles and documents
Ag(I)-C-H Activation Enables Near-Room-Temperature Direct α-Arylation of Benzo[ b]thiophenes
Colletto, Chiara,Panigrahi, Adyasha,Fernández-Casado, Jaime,Larrosa, Igor
, p. 9638 - 9643 (2018/07/21)
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
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Paragraph 0026; 0060, (2018/08/28)
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
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Paragraph 0030; 0074, (2018/09/08)
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.
Three-component 2-aryl substituted benzothiophene formation under transition-metal free conditions
Jiang, Pengcheng,Che, Xingzong,Liao, Yunfeng,Huang, Huawen,Deng, Guo-Jun
, p. 41751 - 41754 (2016/05/24)
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.
Direct arylation of benzo[b]furan and other benzo-fused heterocycles
Dao-Huy, Toan,Haider, Maximilian,Glatz, Fabian,Schnürch, Michael,Mihovilovic, Marko D.
supporting information, p. 8119 - 8125 (2015/01/09)
The direct arylation of benzo[b]furan, benzo[b]thiophene, and indole has been studied by using aromatic bromides as the aryl source. The protocol employing common reagents and a Pd catalyst has led to the regioselective arylation of these heterocycles at the 2-position. A range of functional groups were tolerated, providing quick access to a variety of arylated benzo-fused heterocycles that would be accessible more elaborately using classical synthetic strategies. This is the first systematic study of the direct arylation of benzo[b]-furan.
General method for functionalized polyaryl synthesis via aryne intermediates
Truong, Thanh,Mesgar, Milad,Le, Ky Khac Anh,Daugulis, Olafs
, p. 8568 - 8576 (2014/07/07)
A method for base-promoted arylation of arenes and heterocycles by aryl halides and aryl triflates is described. Additionally, in situ electrophilic trapping of ArLi intermediates generated in the reaction of benzyne with deprotonated arenes or heterocycles has been developed, providing rapid and easy access to a wide range of highly functionalized polyaryls. Base-promoted arylation methodology complements transition-metal-catalyzed direct arylation and allows access to structures that are not easily accessible via other direct arylation methods. The reactions are highly functional-group tolerant, with alkene, ether, dimethylamino, trifluoromethyl, ester, cyano, halide, hydroxyl, and silyl functionalities compatible with reaction conditions.
Palladium-catalyzed C-S coupling: Access to thioethers, benzo[b]thiophenes, and thieno[3,2-b]thiophenes
Kuhn, Marius,Falk, Florian C.,Paradies, Jan
supporting information; experimental part, p. 4100 - 4103 (2011/10/08)
The first C-S bond formation/cross-coupling/cyclization domino reaction using thiourea as a cheap and easy to handle dihydrosulfide surrogate has been developed. Structurally important biarylthioether, benzo[b]thiophenes, and thieno[3,2-b]thiophene scaffolds are provided in high yield.
Selective palladium-catalysed ipso arylation of α,α- disubstituted benzo[b]thien-2-ylmethanols with aryl bromides using PCy 3 as ligand
Biro, A. Beatrix,Kotschy, Andras
, p. 1364 - 1368 (2008/09/18)
α,α-Diphenylbenzo[b]thien-2-ylmethanol was treated with a series of aryl bromides in the presence of palladium(II) acetate and tricyclohexylphosphane to give the appropriate 2-aryl-benzo[b]thiophenes in good to excellent yield with concomitant formation o
