28540-36-5

Upstream product

• 1142-19-4 4,4'-dichlorodiphenyl disulfide 
• 119072-55-8 tert-butylisonitrile 
• 536-74-3 phenylacetylene 
• 20532-33-6 5-chlorobenzothiophene 
• 109674-45-5 4-methyl-2,6-dioxo-8-phenylhexahydro-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide 
• 65520-25-4 5-chloro-benzo[b]thiophen-3-ol 
• 849403-96-9 trifluoro-methanesulfonic acid 5-chloro-benzo[b]thiophen-3-yl ester 
• 98-80-6 phenylboronic acid 
• 7031-25-6 2-(4'-chlorophenylmercapto)acetyl chloride 
• 3405-88-7 (4-chlorophenylthio)acetic acid 

Downstream Products

• 30161-03-6 1-Butylsulfanyl-4-chloro-2-phenylethynyl-benzene 
• 849403-88-9 5-chloro-2-fluoro-3-phenylbenzothiophene 

Relevant academic research and scientific papers

Palladium-catalyzed phosphine-free direct C-H arylation of benzothiophenes and benzofurans involving MIDA boronates

With high regioselectivity, a series of benzoheterocyclic compounds were synthesized via palladiium-catalyzed phosphine-free C-H arylation of benzothiophenes/benzofurans with aryl MIDA boronates at 30-50 °C in moderate to excellent yields. MIDA boronates were used in C-H arylation of heterocycles for the first time. Under the optimal conditions, the benzothiophenes could be transformed into the β-arylbenzothiophenes, and the benzofurans gave only α-aryl-substituted products.

Aromatic ring-opening of 2-fluorobenzothiophenes by alkyllithiums

Diphenylacetylenes are obtained when alkyllithium reagents are added to 3-aryl-2-fluorobenzothiophenes at low temperature. The aromatic ring-opening mechanism involves a nucleophilic addition of the alkyllithium to the sulfur atom of the thiophene. The re

Radical Addition to Isonitriles: A Route to Polyfunctionalized Alkenes through a Novel Three-Component Radical Cascade Reaction

The reaction of aromatic disulfides, alkynes, and isonitriles under photolytic conditions affords polyfunctionalized alkenes - β-arylthio-substituted acrylamides or acrylonitriles - in fair yields through a novel three-component radical cascade reaction. The procedure entails addition of a sulfanyl radical to the alkyne followed by attack of the resulting vinyl radical to the isonitrile. A fast reaction, e.g., scavenging by a nitro derivative or β-fragmentation, is necessary in order to trap the final imidoyl radical, since addition of vinyl radicals to isonitriles seems to be a reversible process. The stereochemistry of the reaction is discussed, particularly with respect to the stereochemical outcome of related hydrogen abstraction reactions by the same vinyl radicals. The lower or even inverted preference for either geometrical isomer observed in our cases with respect to that encountered in hydrogen abstraction reactions is explained in terms of transition-state interactions and/or isomerization of the final imidoyl radical. The latter possibility is supported by semiempirical calculations, which show that the spin distribution in the imidoyl radical can allow rotation of the adjacent carbon - carbon double bond prior to β-fragmentation.