31908-20-0

Upstream product

• 583-55-1 1-Bromo-2-iodobenzene 
• 108-94-1 cyclohexanone 

Downstream Products

• 13130-19-3 1,2,3,4-tetrahydrodibenzo[b,d]furan 
• 35682-32-7 ((4aR,9aR)-1,2,3,4,4a,9a-hexahydro-9H-carbazol-9-yl)(phenyl)methanone 
• 31916-20-8 (-)-2-(o-Bromphenyl)cyclohexanon 
• 31908-21-1 (-)-trans-2-(o-Bromphenyl)-cyclohexanol 
• 205642-01-9 9-(toluene-4-sulphonyl)-2,3,4,9-tetrahydro-1H-carbazole 
• 13815-70-8 phenyl (1,2,3,4-tetrahydro-9H-carbazol-9-yl) methanone 
• 17017-63-9 9-benzyl-2,3,4,9-tetrahydro-1H-carbazole 
• 847355-61-7 9-cyclohexyl-2,3,4,9-tetrahydro-1H-carbazole 
• 86844-02-2 9-phenyl-6,7,8,9-tetrahydro-5H-carbazole 
• 55542-91-1 9-(4-chlorophenyl)-2,3,4,9-tetrahydro-1H-carbazole 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 55542-90-0 9-(4-methoxyphenyl)-2,3,4,9-tetrahydro-1H-carbazole 
• 16587-33-0 1,2,3,4-tetrahydrodibenzothiophene 
• 823787-34-4 2-(2-bromophenyl)-cyclohexanethione 

Relevant academic research and scientific papers

Palladium-catalysed intramolecular enolate O-arylation and thio-enolate S-arylation: synthesis of benzo[b]furans and benzo[b]thiophenes

Enolates derived from α-(ortho-haloaryl)-substituted ketones undergo palladium-catalysed C-O bond formation to deliver benzofuran products in good yield. A catalyst generated from Pd2(dba)3 and the ligand DPEphos effects the key bond

Indoles synthesized from amines via copper catalysis

N-Substituted indoles are synthesized from primary amines through a tandem reaction sequence. Initial condensation of the amine with an α-(o-haloaryl)ketone or aldehyde is followed by intramolecular aryl amination catalyzed by CuI. A variety of anilines and alkyl amines, including those with significant steric demands, are converted to indoles in high yields and with varying indole substitution.

Iron and copper salts in the synthesis of benzo[b]furans

Intramolecular C-O bond forming reactions of aryl 2-bromobenzyl ketones lead to benzo[b]furans. The cyclizations can be catalyzed by 10 mol% of iron trichloride (of 98% or of 99.995% purity) or sub-mol% quantities of copper(II) chloride (of 99.995% purity

On-water chemistry: Copper-catalyzed straightforward synthesis of benzo[b]furan derivatives in neat water

A more sustainable protocol leading to 2-alkyl- or 2-aryl-substituted benzo[b]furans is reported, involving a copper-TMEDA complex which catalyzes the transformation of readily available ketone derivatives into the corresponding benzofurans in good to excellent yields. The reaction is accomplished using water as the solvent without organic cosolvents, and one example of catalyst reutilization is also presented.

Palladium-catalyzed tandem alkenyl and aryl C-N bond formation: A cascade N-annulation route to 1-functionalized indoles

(Chemical Equation Presented) A single tandem operation allows rapid access to a variety of substituted N-functionalized indoles. The nitrogen atom of the indole nucleus is incorporated through Pd-catalyzed aryl and alkenyl C-N bond-forming reactions (see scheme; dba = dibenzylideneacetone). Amine, aniline, amide, carbamate, and sulfonamide functional groups can be introduced efficiently.

Palladium-catalyzed intramolecular O-arylation of enolates: Application to benzo[6]furan synthesis

(Chemical Equation Presented) A catalyst generated from Pd 2(dba)3 and the ligand DPEphos effects intramolecular C-O bond formation between enolates and aryl halides in the conversion of 1-(2-haloaryl)ketones directly into the corres