2340-22-9

Upstream product

• 138950-23-9 2-chloro-3,3,3-trifluoropropiophenone 
• 100-42-5 styrene 
• 887144-94-7 Togni's reagent II 
• 2926-29-6 Langlois reagent 
• 75-63-8 Bromotrifluoromethane 
• 591-51-5 phenyllithium 
• 2314-97-8 iodotrifluoromethane 
• 709-21-7 3,3,3-trifluoro-1-phenylpropan-1-one 
• 103654-96-2 1-(α,α-dichloro-β,β,β-trifluoroethyl)benzylalcohol 
• 1961266-44-3 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate 
• 100-52-7 benzaldehyde 

Downstream Products

• 3238-20-8 (1-bromo-3,3,3-trifluoropropyl)benzene 

Relevant academic research and scientific papers

Copper-Catalyzed three-component oxytrifluoromethylation of alkenes with sodium trifluoromethanesulfinate and hydroxamic acid

Radical paths: The title reaction of olefins with NaSO2CF 3 and N-hydroxy-N-phenylacetamide at room temperature is described for the first time (see scheme). This reaction provides a practical and convenient route to a series of trifluoromethylated alcohols bearing a wide range of functional groups. Copyright

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.

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.

PYRIDAZINONES AND METHODS OF USE THEREOF

Disclosed are compounds according to Formula (A), and related tautomers and pharmaceutical compositions. Also disclosed are therapeutic methods, e.g., of treating kidney diseases, using the compounds of Formula (A).

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.

Powerful, Thermally Stable, One-Pot-Preparable, and Recyclable Electrophilic Trifluoromethylating Agents: 2,8-Difluoro- and 2,3,7,8-Tetrafluoro-S-(trifluoromethyl)dibenzothiophenium Salts

Although many electrophilic trifluoromethylating agents have been reported to date, practically useful reagents have yet to be developed. S-(Trifluoromethyl)dibenzothiophenium salts, known as Umemoto's reagents, have two significant drawbacks that have ha

Why does alkylation of the N-H functionality within M/NH bifunctional Noyori-type catalysts lead to turnover?

Molecular metal/NH bifunctional Noyori-type catalysts are remarkable in that they are among the most efficient artificial catalysts developed to date for the hydrogenation of carbonyl functionalities (loadings up to ～10-5 mol %). In addition, these catalysts typically exhibit high C=0/C=C chemo- and enantioselectivities. This unique set of properties is traditionally associated with the operation of an unconventional mechanism for homogeneous catalysts in which the chelating ligand plays a key role in facilitating the catalytic reaction and enabling the aforementioned selectivities by delivering/accepting a proton (H+) via its N-H bond cleavage/formation. A recently revised mechanism of the Noyori hydrogenation reaction (Dub, P. A et al. J. Am. Chem. Soc. 2014,136,3505) suggests that the N-H bond is not cleaved but serves to stabilize the turnover-determining transition states (TDTSs) via strong N-H···O hydrogen-bonding interactions (HBIs). The present paper shows that this is consistent with the largely ignored experimental fact that alkylation of the N-H functionality within M/NH bifunctional Noyori-type catalysts leads to detrimental catalytic activity. The purpose of this work is to demonstrate that decreasing the strength of this HBI, ultimately to the limit of its complete absence, are conditions under which the same alkylation may lead to beneficial catalytic activity.

Radical-polar crossover reactions of vinylboron ate complexes

Vinyl boronic esters are valuable substrates for Suzuki-Miyaura cross-coupling reactions. However, boron-substituted alkenes have drawn little attention as radical acceptors, and the radical chemistry of vinylboron ate complexes is underexplored. We show here that carbon radicals add efficiently to vinylboron ate complexes and that their adduct radical anions undergo radical-polar crossover: A 1,2-alkyl/aryl shift from boron to the α-carbon sp2 center provides secondary or tertiary alkyl boronic esters. In contrast to the Suzuki-Miyaura coupling, a transition metal is not required, and two carbon-carbon bonds are formed. The valuable boronic ester moiety remains in the product and can be used in follow-up chemistry, enlarging the chemical space of the method. The cascade uses commercial starting materials and provides access to perfluoroalkylated alcohols, γ-lactones, γ-hydroxy alkylnitriles, and compounds bearing quaternary carbon centers.

POLYDENTATE LIGANDS AND THEIR COMPLEXES FOR MOLECULAR CATALYSIS

The present invention relates generally to novel achiral and chiral sulfur-, nitrogen- and phosphorus-containing ligands, designated as NNS-type, P(0)NS-type, PNS-type, SNNS-type, SNNP(0)-type, or SNNP-type polydentate ligands and transition metal complexes of these ligands. The catalysts derived from these ligands and transition metal complexes may be used in a wide range of catalytic reactions, including hydrogenation and transfer hydrogenation of unsaturated organic compounds, dehydrogenation of alcohols and boranes, various dehydrogenative couplings, and other catalytic transformations.