1353568-97-4

Upstream product

• 56572-25-9 2-(trifluoromethylsulfonyl)-N-tert-butoxycarbonylhydrazine 
• 2918-91-4 N,N-diphenyl methacrylamide 
• 129946-88-9 Umemoto's reagent 
• 62-53-3 aniline 
• 1611-83-2 2-methyl-N-phenylacrylamide 
• 122-39-4 diphenylamine 
• 421-83-0 trifluoromethane sulfonyl chloride 
• 2926-29-6 Langlois reagent 
• 2926-30-9 sodium triflate 
• 887144-94-7 Togni's reagent II 
• 81290-20-2 (trifluoromethyl)trimethylsilane 

Relevant academic research and scientific papers

Catalyst-free, direct electrochemical trifluoromethylation/cyclization of N-arylacrylamides using TfNHNHBoc as a CF3 source

A new electrochemical strategy for trifluoromethylation/cyclization using TfNHNHBoc as a CF3 source was established. This approach was realized by the direct electrolysis of TfNHNHBoc under external oxidant-free and catalyst-free conditions, and afforded various trifluoromethylated oxindoles with good functional group compatibility and broad substrate scope. Preliminary mechanistic studies show that the reaction proceeds by a radical process.

Visible-light-induced trifluoromethylation of N-aryl acrylamides: A convenient and effective method to synthesize CF3-containing oxindoles bearing a quaternary carbon center

The incorporation of the trifluoromethyl group into organic molecules has becoming a hot topic, as trifluoro-methylated compounds possess unique physical properties and biological activities. The catalytic cycle may involve a cationic intermediate whose stability was effected by the substituents on the aromatic ring and that the process of generating this cationic intermediate may be the rate limiting. To demonstrate the scalability of this protocol, the reaction was carried out on a mole scale under the standard reaction conditions. The reaction could also be obtained with a moderate yield. Control experiments indicated that both light and photocatalyst were essential to the success of the tandem trifluoromethylation/arylation reaction.

A metal-free route to CF3-containing oxindoles by PhI(OAc) 2-mediated trifluoromethylation of N-arylacrylamides with TMSCF 3

A mild and efficient PhI(OAc)2-mediated trifluoromethylation reaction of N-arylacrylamides with TMSCF3 under metal-free conditions was developed. This method provides convenient access to a variety of useful CF3-containing

Concise synthesis of oxindole derivatives bearing a 3-trifluoroethyl group: Copper-catalyzed trifluoromethylation of acryloanilides

Carbotrifluoromethylation of acryloanilide derivatives with the combination of CuI and Togni's reagent affords oxindole derivatives bearing a 3-trifluoroethyl group in high yields under mild conditions that are compatible with various functional groups.

Synthesis of oxindoles through trifluoromethylation of: N -aryl acrylamides by photoredox catalysis

Mild and direct intramolecular oxidative aryltrifluoromethylations of activated alkenes have been established through visible light photocatalysis, affording a range of CF3-containing oxindoles or isoquinolinediones in the presence of an organic fluorophore-type photocatalyst 4CzIPN, oxygen and visible light irradiation under strong oxidant and transition metal free conditions. A variety of frequently encountered functional groups are well tolerated in this transformation.

Copper-catalyzed trifluoromethylation of N-arylacrylamides on water at room temperature

A copper-catalyzed intramolecular trifluoromethylation of arylacrylamides leads to oxindole derivatives, effected with stable and inexpensive Langlois' reagent (CF3SO2Na). These reactions proceed via a radical process in water at room temperature. The aqueous solution can be recycled. This journal is

Silver-mediated radical trifluoromethylarylation of activated alkenes for the synthesis of oxindoles bearing a CF3 group

A radical trifluoromethylarylation of N-arylacrylamides with in situ generated [AgCF3] species from Me3SiCF3 and AgF in DMF is established through a tandem radical addition and C-H activation pathway. It provided a concise

Metal-free trifluoromethylation and arylation of alkenes: Domino synthesis of oxindole derivatives

A novel, simple and highly efficient method for the synthesis of 3-(trifluoromethyl)-indolin-2-one derivatives has been developed. The protocol uses readily available N-alkyl-N-phenylacrylamides as the starting materials, inexpensive and easily stored Langlois reagent (sodium trifluoromethanesulfinate) as the trifluoromethyl source, and iodobenzene diacetate [PhI(OAc)2] as the oxidant. The procedure involves a metal-free domino trifluoromethylation and arylation of alkenes. The methods did not need mediation of any transition metal which avoided contaminations of toxic metals in the products.

Exploring the Structure and Performance of Cd–Chalcogenide Photocatalysts in Selective Trifluoromethylation

The field of heterogeneous photoredox catalysis has grown substantially and impacted organic synthesis because of the affordability and reusability of catalysts. This study reports radical trifluoromethylation with Cd–chalcogenide semiconductors. Cd semiconductors, particularly CdSe, are readily available, commercial, visible-light-responsive, heterogeneous photocatalysts. The potential of readily available Cd semiconductors, particularly CdSe, is confirmed by their increased photocatalytic activity toward trifluoromethylation with various substrates, such as (hetero)arenes and vinylic amides/acids, via addition, cyclization, and decarboxylation under visible light. The economic significance of this strategy is also highlighted through the scalable synthesis of biologically active molecules followed by catalyst reuse. Moreover, these catalysts are relatively inexpensive compared with transition metal-based homogeneous photocatalysts, presently used in organic synthesis.

Electrochemical trifluoromethylation/cyclization for the synthesis of isoquinoline-1,3-diones and oxindoles

Herein, we describe a protocol for electrochemical cathode reduction to generate trifluoromethyl radicals. The trifluoromethylation reagent (IMDN-SO2CF3) used in this strategy is inexpensive and easy to obtain, and the reaction can be conducted efficiently without the addition of additional redox reagents. Using this strategy, we achieved electrochemical trifluoromethylation/cyclization for the synthesis of isoquinoline-1,3-diones and oxindoles. This protocol has good functional group tolerance and a broad substrate scope.