88486-65-1Relevant academic research and scientific papers
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.
Sunlight-driven trifluoromethylation of olefinic substrates by photoredox catalysis: A green organic process
Akita, Munetaka,Koike, Takashi
, p. 742 - 751 (2015/07/15)
The principles and utility of photoredox catalysis in organic synthesis are described. After a brief description of the features of the two types of catalytic photoredox processes following the reductive quenching cycle (RQC) and the oxidative quenching cycle (OQC), the discussion is focused on organic transformations based on OQC, in particular the trifluoromethylation of olefinic substrates with electrophilic trifluoromethylating reagents furnishing solvolytic addition products and substitution products. It is concluded that catalytic photoredox systems are green from the point of view of harmfulness, safety, and energy source (visible light, including sunlight). Future prospects of photoredox catalysis will be also discussed.
Three-component oxytrifluoromethylation of alkenes: Highly efficient and regioselective difunctionalization of C=C bonds mediated by photoredox catalysts
Yasu, Yusuke,Koike, Takashi,Akita, Munetaka
supporting information, p. 9567 - 9571 (2012/11/07)
Here comes the sun: A facile vicinal difunctionalization of alkenes, oxytrifluoromethylation, was established by visible-light-driven photoredox catalysis. Judicious choice of the CF3 source is key. Nucleophiles such as water, alcohols, and carboxylic acids can be used in this highly efficient (2-4 h) and regioselective (100 %) transformation using light-emitting diode (LED) lamps and natural sunlight. SET=single-electron transfer. Copyright
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
