13541-19-0

Upstream product

• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 2926-29-6 Langlois reagent 
• 2314-97-8 iodotrifluoromethane 
• 75-63-8 Bromotrifluoromethane 
• 122948-58-7 1-(4-bromophenyl)vinyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Redox-Neutral Tetrafluoroethylation of Aryl Alkynes with 1,1,2,2-Tetrafluoroethane Sulfonic Acid Leading to α-Tetrafluoroethylated Acetophenones

The redox-neutral tetrafluoroethylation of alkynes with 1,1,2,2-tetrafluroroethanesulfonic acid (TFESA) and azobis(isobutyronitrile) (AIBN) proceeds via the formation of vinyl tetrafluoroethanesulfonates followed by a radical tetrafluoroethylation. Experimental and theoretical results support an intermolecular reaction.

Cobalt-Tertiary-Amine-Mediated Hydroxytrifluoromethylation of Alkenes with CF3Br and Atmospheric Oxygen

The mild and efficient hydroxytrifluoromethylation of alkenes with bromotrifluoromethane (CF3Br) and atmospheric oxygen mediated by cobalt-tertiary amine is described. This reaction proceeds with broad substrate scope and good functional group compatibility. Mechanistic studies indicate that the reaction proceeds through a radical pathway, which is enabled by combination of the previously unexplored highly efficient N-isopropyl-N,2-dimethylpropan-2-amine with Co(II) for the single electron reduction of CF3Br to CF3 radical.

Method for preparing hydroxyl and trifluoromethyl substituted compounds through reaction of olefin and trifluo-romethyl bromide

The invention discloses a method for preparing hydroxyl and trifluoromethyl substituted compounds through olefin addition reaction. According to the method, a compound containing carbon-carbon doublebonds and trifluo-romethyl bromide are taken as raw materials, a metal salt-tertiary amine system is taken as a catalyst, air is taken as an oxidizing agent, carbon-carbon double bonds can be subjected to addition reaction, and compounds with hydroxyl substitution and trifluoromethyl substitution at the same time are prepared; wherein the metal salt is one or more selected from a cobalt salt, a silver salt, a bismuth salt, a nickel salt, an iron salt or a copper salt; the tertiary amine is N-isopropyl-N-methyl-tert-butylamine or N, N-diisopropylethylamine. According to the method, the metal salt-tertiary amine system is taken as a catalyst for the first time, hydroxyl substitution and trifluoromethyl substitution of olefins are realized, one-step reaction is enough, reaction process conditions are mild, reaction raw materials are cheap and easily available, cost is low, reaction substrates have strong applicability, and can participate in the reaction as long as carbon-carbon double bonds exist in the structures, and are not influenced by substituent groups on double bond carbon atoms, and the product yield is high.

Catalyst-Free Hydroxytrifluoromethylation of Alkenes UsingIodotrifluoromethane

The importance of CF3-containing molecules in pharmaceuticals, agrochemicals and materials intrigues the intense interest in synthetic methodology of these compounds. With a purpose to enrich trifluoromethylation methodology, we carefully exami

Catalyst-Free Oxytrifluoromethylation of Alkenes through Paired Electrolysis in Organic-Aqueous Media

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

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

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.

A practical method for metal-free radical trifluoromethylation of styrenes with NaSO2CF3

A mild and practical protocol for the metal-free trifluoromethylation of styrenes using NaSO2CF3 (Langlois reagent) and TBHP was developed. The approach provides efficient access to α-trifluoromethylated ketones and alcohols in moderate to good yields. Georg Thieme Verlag Stuttgart New York.

Three-component oxytrifluoromethylation of alkenes: Highly efficient and regioselective difunctionalization of C=C bonds mediated by photoredox catalysts

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