88486-65-1Relevant articles and documents
Catalyst-Free Oxytrifluoromethylation of Alkenes through Paired Electrolysis in Organic-Aqueous Media
Jud, Wolfgang,Kappe, C. Oliver,Cantillo, David
supporting information, p. 17234 - 17238 (2018/11/10)
A mild, catalyst-free electrochemical oxytrifluoromethylation of alkenes has been developed. The procedure is based on the paired electrolysis of sodium triflinate and water in an undivided cell. Anodic oxidation of the triflinate anion generates trifluoromethyl radicals that react with the alkene. Water plays a dual role as oxidant for the cathode and nucleophile. The method has been utilized to prepare a diverse set of 1-hydroxy-2-trifluoromethyl compounds in moderate to excellent yields (27–94 %). Alcohols have also been tested as nucleophiles for this versatile method with moderate yields. Facile recycling of the electrolyte has been demonstrated, and application of electricity avoids the use of stoichiometric amounts of oxidizers in a safe and environmentally benign reaction.
Manganese-Catalyzed Aerobic Oxytrifluoromethylation of Styrene Derivatives Using CF3SO2Na as the Trifluoromethyl Source
Yang, Yi,Liu, Yingle,Jiang, Yan,Zhang, Yu,Vicic, David A.
, p. 6639 - 6648 (2015/10/06)
A mild and practical protocol for manganese-catalyzed aerobic oxytrifluoromethylation of olefinic bonds of styrene derivatives using CF3SO2Na (Langlois reagent) as the CF3 source is described. A distinguishing feature of this method is the generation of trifluoromethyl radicals from CF3SO2Na using the simple manganese salt/O2 system. The reaction proceeds under ambient conditions, free of added peroxide initiators, and provides moderate to good selectivities for alcohol versus ketone product.
In situ generation of 3,3,3-trifluoropropanal and its use for carbon-carbon bond-forming reactions
Yamazaki, Takashi,Kobayashi, Rei,Kitazume, Tomoya,Kubota, Toshio
, p. 2499 - 2502 (2007/10/03)
The DIBAL reduction of 2-phenylethyl 3,3,3-trifluoro-2-methylpropionate 2 at -78 °C afforded the aluminum acetal 3, and this intermediate, on worming up to 0 °C, was found to slowly decompose into the corresponding aldehyde 4, which smoothly reacted with