1353568-92-9

Upstream product

• 100-61-8 N-methylaniline 
• 15796-89-1 N-methyl-N-phenylmethacrylamide 
• 1611-83-2 2-methyl-N-phenylacrylamide 
• 62-53-3 aniline 
• 6273-94-5 N-methyl-N-phenylacrylamide 
• 136918-14-4 phthalimide 
• 1353568-86-1 2-(hydroxymethyl)-N-methyl-N-phenylacrylamide 
• 74-88-4 methyl iodide 

Downstream Products

• 1587688-97-8 C₂₆H₂₀F₂N₂O₅S 

Relevant academic research and scientific papers

Catalyst-free and selective trifluoromethylative cyclization of acryloanilides using PhICF3Cl

Trifluoromethylation-triggered cyclization of alkenes provides a useful route to CF3-containing cyclic compounds. Current approaches to generate CF3-based initiators from a CF3 source require a catalyst or an activator. This work describes a catalyst-free protocol to innately produce electrophilic CF3 species from PhICF3Cl for trifluoromethylative cyclization of acryloanilides. A new domino biscyclization of dienes has been developed leading to trifluoroethylated tetrahydroindenoquinolinones with chemo- and stereo-selectivity.

Disulfides as Sulfonylating Precursors for the Synthesis of Sulfone-Containing Oxindoles

The first facile one-pot synthesis of sulfone-containing oxindoles with easily accessible disulfides as the sulfonylating precursors is described. This reaction occurs smoothly under transition metal-free conditions and shows excellent functional group tolerance, allowing the facile and efficient green synthesis of various sulfone-containing oxindoles in aqueous solution. Preliminary mechanistic studies reveal that both water (H2O) and potassium persulfate (K2S2O8) can be the oxygen source of the sulfone groups in the products. (Figure presented.).

Light-induced BiOBr nanosheets accelerated highly regioselective intermolecular trifluoromethylation/arylation of alkenes to synthesize CF3-containing aza-heterocycles

A light-induced, BiOBr nanosheets accelerated intermolecular one-pot tandem trifluoromethylation/arylation of alkenes was presented. With this method, a series of CF3-containing aza-heterocycles with high selectivity were fabricated in moderate to good yields. Preliminary mechanistic studies revealed that the exceptional transformation was originated from the synergistic effect of photogenerated electrons and holes. Density function theory (DFT) was adopted to understand the high selectivity of this photocatalytic chemical transformation.

Arylnitration of alkenes by nitration/C-H functionalization cascade using AgNO3 and HOAc

A novel arylnitration of alkenes by nitration and C-H functionalization cascade process has been developed. This methodology provides an efficient way to construct a variety of nitro-containing oxindoles and dihydroquinolin-2(1H)- ones. In addition, the process exhibits significant functional group tolerance. Moreover, the use of inexpensive and readily available starting materials makes this practical and atom-economical approach particularly attractive.

Synthesis of oxindoles through silver-catalyzed trifluoromethylation-, difluoromethylation- and arylsulfonylation-cyclization reaction of N-arylacrylamides

Efficient synthesis of trifluoromethyl and difluoromethyl-substituted oxindoles was achieved by reacting Langlois reagent or Baran reagent with N-arylacrylamides. However, the reaction of aryl sulfinic acid sodium salts with N-arylacrylamides did not give the desulfinative products, instead, aryl sulfonated products were produced. Copyright

Arylnitration of alkenes by nitration/C-H functionalization cascade using AgNO3 and HOAc

A novel arylnitration of alkenes by nitration and C-H functionalization cascade process has been developed. This methodology provides an efficient way to construct a variety of nitro-containing oxindoles and dihydroquinolin-2(1H)-ones. In addition, the process exhibits significant functional group tolerance. Moreover, the use of inexpensive and readily available starting materials makes this practical and atom-economical approach particularly attractive.

Direct annulations toward phosphorylated oxindoles: Silver-catalyzed carbon-phosphorus functionalization of alkenes

Silver screen: The AgNO3-catalyzed carbon phosphorylation of alkenes occurs by an alkene addition/cyclization cascade. Ag+ reacts with Ph2P(O)H to form the crucial active intermediate 1, which promotes the reaction. This method requires a cheap, nontoxic silver salt as the catalyst and substrates for the transformation are simple and readily accessible.

Metal-free carbonitration of alkenes using K2S2O 8

A novel metal-free oxidative carbonitration of alkenes by a nitration and C-H functionalization cascade process has been developed. This methodology provides an efficient way to construct valuable nitro-containing oxindoles.

Palladium-catalyzed oxidative aryltrifluoromethylation of activated alkenes at room temperature

A palladium-catalyzed intramolecular oxidative aryltrifluoromethylation reaction of activated alkenes has been explored. The reaction allows for an efficient synthesis of a variety of CF3-containing oxindoles. Preliminary mechanistic study indicated that the reaction involves a Csp 3-PdIV(CF3) intermediate, which undergoes reductive elimination to afford a Csp3-CF3 bond.

Palladium-catalyzed oxidative arylalkylation of activated alkenes: Dual C-H bond cleavage of an arene and acetonitrile

Not one but two: The title reaction proceeds through the dual C-H bond cleavage of both aniline and acetonitrile (see scheme). The reaction affords a variety of cyano-bearing indolinones in excellent yield. Mechanistic studies demonstrate that this reaction involves a fast arylation of the olefin and a rate-determining C-H activation of the acetonitrile. Copyright