1263875-74-6

Upstream product

• 603-76-9 1-methylindole 
• 583-55-1 1-Bromo-2-iodobenzene 
• 683229-61-0 1-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole 
• 2905-25-1 o-bromobenzenesulfonyl chloride 

Relevant academic research and scientific papers

An Expedient Procedure for the Synthesis of Benzo[4,5]silolo[2,3-b]thiophenes and Related Systems

The straightforward assembly of various thiophene-fused benzosiloles is accomplished by 2-fold metalation of benzo[b]thiophenes substituted at C3 with ortho-brominated aryl groups followed by electrophilic substitution with dichlorosilanes. The method relies on the innate acidity of the C(sp2)-H bond at C2 of benzo[b]thiophenes and the halogen-metal exchange of the proximal C(sp2)-Br bond. The related indole- and benzofuran-annulated systems are also accessible, but these siloles are chemically less stable. An example of a thiophene-fused benzogermole is included as well.

Eco-friendly solvents for palladium-catalyzed desulfitative C-H bond arylation of heteroarenes

Herein, we report the Pd-catalyzed regioselective direct arylation of heteroarenes in which benzenesulfonyl chlorides are used as coupling partners through a desulfitative cross-coupling that can be performed in diethyl carbonate (DEC) or cyclopentyl methyl ether (CPME) as green and renewable solvents or even in neat conditions instead of dioxane or dimethylacetamide (DMA). Under these solvent conditions, the reaction proceeds with a wide range of heteroarenes. C2- or C5-arylated products were obtained with furan and pyrrole derivatives. Benzofuran was also arylated regioselectively at the C2-position, whereas the reaction proceeds selectively at the C3- or C4-positions if thiophenes and benzothiophenes are used. Moreover, in some cases, especially with 1-methylindole, solvent-free conditions afforded better regioselectivities and/or yields than the reaction performed in the presence of solvents.

Cascade carbopalladation-annulation approach toward polycylic derivatives of indole and indolizine

A convenient method for construction of polycyclic fused nitrogen-containing heterocycles has been developed. The methodology involves palladium-catalyzed intermolecular carbopalladation-annulation cascade reaction of haloaryl heterocyclic derivatives with different alkynes under relatively mild reaction conditions. Thus, the palladium-catalyzed cascade cyclization of bromophenyl derivatives of indolizine and indole with alkynes afforded tetracycles, possessing a newly formed fused six-membered ring. The reaction of 3-(2-iodobenzyl)-indoles with a variety of alkynes afforded polycyclic compounds with fused seven-membered rings. Annulation with unsymmetrical alkynes exhibited varied regioselectivity. Overall, this approach allows for quick and efficient assembly of polycyclic derivatives of indole and indolizine from easily available precursors. ARKAT-USA, Inc.