1228320-13-5

Upstream product

• 50562-79-3 1-(4-tolylsulfonyl)indole-3-carboxaldehyde 
• 64-19-7 acetic acid 
• 108-24-7 acetic anhydride 
• 67593-11-7 1-[(4-methylphenyl)sulfonyl]indol-3-ylmethanol 
• 487-89-8 Indole-3-carboxaldehyde 
• 98-59-9 p-toluenesulfonyl chloride 
• 75-36-5 acetyl chloride 
• 3240-34-4 [bis(acetoxy)iodo]benzene 
• 915706-91-1 2-(1-tosyl-1H-indol-3-yl)acetyl chloride 
• 128742-77-8 [N-(p-toluenesulfonyl)indol-3-yl]acetic acid 
• 947689-42-1 N-(2-iodophenyl)-4-methyl-N-(propa-1,2-dien-1-yl)benzenesulfonamide 
• 127-09-3 sodium acetate 

Relevant academic research and scientific papers

Synthesis of Indole/Benzofuran-Containing Diarylmethanes through Palladium-Catalyzed Reaction of Indolylmethyl or Benzofuranylmethyl Acetates with Boronic Acids

The palladium-catalyzed synthesis of indole/benzofurancontaining diarylmethanes starting from indolylmethyl or benzofuranylmethyl acetates with boronic acids has been investigated. The success of the reaction is influenced by the choice of precatalyst: with indolylmethyl acetates the reaction works well with [Pd(η3-C3H5)Cl]2/XPhos while with benzofuranylmethyl acetates Pd2(dba)3/XPhos is more efficient. The good to high yields and the simplicity of the experimental procedure make this protocol a versatile synthetic tool for the preparation of 2- and 3-substituted indoles and 2-benzo[b]furans. The methodology can be advantageously extended to the preparation of a key precursor of Zafirlukast.

Proton-exchanged montmorillonite-mediated reactions of hetero-benzyl acetates: Application to the synthesis of Zafirlukast

Proton-exchanged montmorillonite (H-mont) with outstanding surface characteristics can provide abundant acidic sites in the mesopores, and serve as an efficient heterogeneous catalyst for the synthesis of heterocycle-containing diarylmethanes via Friedel-Crafts-like alkylation of (hetero)arenes by heterobenzyl acetates under mild reaction conditions without requiring any additives or an inert atmosphere. Using this strategy, the gram-scale synthesis of indole-containing diarylmethane 13 has been accomplished in good yield for the preparation of Zafirlukast. In addition, H-mont can be applied to the nucleophilic substitution reactions of heterobenzyl acetate 5p with a variety of alcohols and 1,3-dicarbonyl compounds.

Palladium-Catalyzed 2-(Neopentylsulfinyl)aniline Directed C–H Acetoxylation and Alkenylation of Arylacetamides

The 2-(neopentylsulfinyl)aniline directing group that promotes rapid palladium-catalyzed C–H acetoxylation and alkenylation of arylacetamides has been developed. The acetoxylation reaches completion within only 40 min at 100 °C and leads to the bis-functionalized products. Alternatively, the reaction can be carried out at room temperature, which is beneficial for sensitive substrates. For the alkenylation, we have developed a protocol in which easily available 1-substituted cyclopropanols were employed as equivalents of vinyl ketones.

Synthesis of allyl acetates via palladium-catalysed functionalisation of allenes and 1,3-dienes

-Allylpalladium intermediates are known to participate efficiently in transformations involving nucleophilic species. Exploring these processes, we have developed a method for the preparation of allyl acetates via palladium-catalysed functionalisation of

Trialkylsilyl triflimides as easily tunable organocatalysts for allylation and benzylation of silyl carbon nucleophiles with non-genotoxic reagents

Trialkylsilyl triflimides generated in situ are unique catalysts for the electrophilic benzylation or allylation of trialkylsilylenol ethers or allyl trialkylsilanes with non-genotoxic alkylating reagents such as benzyl and allyl acetates. In most cases the reactions are fast at room temperature and yields are high. The reaction works particularly well with electron-rich benzyl donors including derivatives of pyrrole, indole and furane.