403-68-9Relevant academic research and scientific papers
Metal-free trifluoromethylthiolation of arenediazonium salts with Me4NSCF3
Bertoli, Giulia,Exner, Benjamin,Evers, Mathies V.,Tschulik, Kristina,Goo?en, Lukas J.
, p. 132 - 136 (2018/04/05)
A metal-free entry to the pharmaceutically meaningful substrate class of trifluoromethyl thioethers has been developed starting from widely available arenediazonium salts and commercially available Me4N+SCF3?. This reaction proceeds within one hour at 0 °C and is applicable to a wide range of functionalized substrates.
Copper-Catalyzed Trifluoromethylthiolation of Di(hetero)aryl-λ3-iodanes: Mechanistic Insight and Application to Synthesis of (Hetero)Aryl Trifluoromethyl Sulfides
Saravanan, Perumal,Anbarasan, Pazhamalai
supporting information, p. 3521 - 3528 (2016/01/25)
The direct and regioselective copper/S-Phos-catalyzed trifluoromethylthiolation of symmetrical and unsymmetrical di(hetero)aryl-λ3-iodanes has been accomplished for the synthesis of various (hetero)aryl trifluoromethyl sulfides employing readily accessible silver trifluoromethylthiolate (AgSCF3) as nucleophilic trifluoromethylthiolating reagent. The developed transformation tolerates various functional groups like nitrile, enolizable ketone, ester, nitro and free carboxylic acid. Interestingly, the formal trifluoromethylthiolation of arenes was also achieved through integration of the synthesis of diaryl-λ3-iodanes from arenes with the trifluoromethylthiolation. Mechanistic investigations did not favor the radical formation and SET pathway. Based on the variable temperature 19F NMR spectroscopy, isolation of the most relevant catalytic intermediate, and stoichiometric studies supported the Cu(I)/Cu(III) catalytic cycle, wherein the oxidative addition of diaryl-λ3-iodanes was assisted by the silver salt.
Convenient synthesis and isolation of trifluoromethylthio-substituted building blocks
Harsányi, Antal,Dorkó, éva,Csapó, ágnes,Bakó, Tibor,Peltz, Csaba,Rábai, József
experimental part, p. 1241 - 1246 (2011/11/12)
Various aryl-, heteroaryl-, and alkyl mercaptanes (RSH, 1a-r) were treated with a slight excess of NaH suspended in DMF to make the appropriate sodium thiolates (RSNa), which then reacted with 1.3 equivalent of CF3I at room temperature for overnight to afford the appropriate trifluoromethyl sulfides (CF3SR, 2) in fair to good yields. The radical chain alkylation reaction was effective without the use of UV irradiation with all but three substrates (thiosalicylic acid, 1k; 2-mercaptobenzimidazole, 1q; and 3-mercaptopropionic acid, 1r). Steam-distillation was found as an effective and easy to upscale means for the isolation of these volatile and water immiscible sulfides. The CF3I reagent gas was conveniently weighed and delivered to the reaction mixture by the balloon technique or as a preliminary made stock solution in DMF or DMSO. The sulfides 2 obtained here were assayed by GC and characterized by 1H, 13C, 19F NMR and MS spectroscopy.
Trifluoromethylthiodediazoniation: A simple, efficient route to trifluoromethyl aryl sulfides
Adams, Dave J.,Goddard, Andrew,Clark, James H.,Macquarrie, Duncan J.
, p. 987 - 988 (2007/10/03)
Copper(I) trifluoromethanethiolate reacts with a range of diazonium salts containing electron-withdrawing groups to give the corresponding trifluoromethyl aryl sulfides in high yield; it is also possible to carry out the diazotisation and trifluoromethylthiolation in one pot directly from the anilines.
