1551041-80-5

Upstream product

• 1417819-63-6 1-azido-2-((4-chlorophenyl)ethynyl)benzene 
• 1211-35-4 2-(4-chlorophenyl)-1H-indole 

Downstream Products

• 2894-51-1 2-amino-4'-chlorobenzophenone 
• 1175713-04-8 tert-butyl 3-(4-chlorophenyl)-2-oxoindoline-1-carboxylate 
• 282549-41-1 3-(4-chlorophenyl)indolin-2-one 
• 1567850-40-1 (S)-tert-butyl 3-(4-chlorophenyl)-3-(trifluoromethanesulfenyl)-2-oxoindoline-1-carboxylate 
• 1588428-31-2 C₁₅H₉ClF₃NOS 

Relevant academic research and scientific papers

Synthetic Studies toward 1,2,3,3a,4,8b-Hexahydropyrrolo[3,2-b]indole Core. Unusual Fragmentation with 1,2-Aryl Shift

Base-assisted transformations of 2-(3-oxoindolin-2-yl)acetonitriles were investigated. Unexpectedly, attempted reactions of substrates possessing nonprotected nitrogen atoms were accompanied by unusual extrusions of 2-arylacetonitriles, followed by a 1,2-aryl shift to afford 3-hydroxyindolin-2-ones. On the other hand, the reactions for N-alkyl derivatives of oxoindolines took the expected route by only providing 1,2,3,3a,4,8b-hexahydropyrrolo[3,2-b]indoles.

Counterion Control of t-BuO-Mediated Single Electron Transfer to Nitrostilbenes to Construct N-Hydroxyindoles or Oxindoles

tert-Butoxide unlocks new reactivity patterns embedded in nitroarenes. Exposure of nitrostilbenes to sodium tert-butoxide was found to produce N-hydroxyindoles at room temperature without an additive. Changing the counterion to potassium changed the reaction outcome to yield solely oxindoles through an unprecedented dioxygen-transfer reaction followed by a 1,2-phenyl migration. Mechanistic experiments established that these reactions proceed via radical intermediates and suggest that counterion coordination controls whether an oxindole or N-hydroxyindole product is formed.

One-Pot Synthesis of 2-Aminobenzophenones from 2-Alkynyl Arylazides Catalyzed by Pd and Cu Precursors

We describe a novel one-pot three-step reaction of 2-alkynyl arylazides through palladium-catalyzed formation of 3-hydroxy-3-phenylindolin-2-ones followed by hydrolysis of amide bonds and copper-catalyzed decarboxylation to give 2-aminobenzophenones. This synthetic method works well with various 2-alkynyl arylazides and affords the products in moderate to good yields under mild reaction conditions.