1417820-89-3

Upstream product

• 98-83-9 isopropenylbenzene 
• 2926-29-6 Langlois reagent 
• 77152-08-0 trifluoromethylcopper(I) 
• 1961266-44-3 2,8-difluoro-5-(trifluoromethyl)-5H-dibenzo[b,d]thiophen-5-ium trifluoromethanesulfonate 
• 75-63-8 Bromotrifluoromethane 

Relevant academic research and scientific papers

NMP and O2 as Radical Initiator: Trifluoromethylation of Alkenes to Tertiary β-Trifluoromethyl Alcohols at Room Temperature

A novel strategy was developed to trigger ·CF3 by using in situ generated peroxide in NMP under O2 or air as the radical initiator. Radical trifluoromethylation of alkenes was achieved toward tertiary β-trifluoromethyl alcohols. Various tertiary β-trifluoromethyl alcohols can be synthesized in good yields without extra oxidants or transition metal catalysts. Preliminary mechanistic investigation revealed that O2 diffusion can influence the reaction rate.

Bifunctional Metal-Organic Layer with Organic Dyes and Iron Centers for Synergistic Photoredox Catalysis

Here we report the design of a bifunctional metal-organic layer (MOL), Hf-EY-Fe, by bridging eosin Y (EY)-capped Hf6 secondary building units (SBUs) with Fe-TPY (TPY = 4′-(4-carboxyphenyl)[2,2′:6′,2′′-terpyridine]-5,5′′-dicarboxylate) ligands. With the organic dye EY as an efficient photosensitizer and TPY-Fe(OTf)2 as the catalytic center, Hf-EY-Fe efficiently catalyzes aminotrifluoromethylation, hydroxytrifluoromethylation, and chlorotrifluoromethylation of alkenes. Hf-EY-Fe also catalyzes the synthesis of CF3-substituted derivatives of large bioactive molecules such as rotenone, estrone, and adapalene with sizes of up to 2.2 nm. The proximity between EY and iron centers and their site isolation in Hf-EY-Fe enhance catalytic activity while inhibiting their mutual deactivation, leading to high turnover numbers of up to 1840 and good recyclability of the MOL catalyst.

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.

A facile method for hydroxytrifluoromethylation of alkenes with Langlois reagent and DMSO

A practical hydroxytrifluoromethylation of alkenes using the Langlois reagent as the trifluoromethyl source and DMSO as the oxidant is described. This reaction is mild and operationally simple, without exclusion of either moisture or oxygen, allowing access to a wide range of β-trifluoromethyl alcohols in useful yields. This transformation is environmentally friendly and can be easily scaled up to gram level.

Photooxidative Keto-Trifluoromethylation of Styrenes by Means of an Anthraquinone-Based Organocatalyst

α-Trifluoromethyl ketones are versatile building blocks for the synthesis of various trifluoromethyl-functionalized molecules. Although there are significant advantages in the development of methods toward direct transformations of styrenes into α-trifluoromethyl ketones, most procedures leading to α-trifluoromethyl ketones require heavy- or transition-metal-based complexes. Herein, a novel method is developed for the synthesis of α-trifluoromethyl ketones via anthraquinone-catalyzed photooxidative keto-trifluoromethylation of styrenes with the readily available Langlois reagent (CF 3 SO 2 Na) under an oxygen atmosphere. The reactions proceed smoothly to give the products in moderate to excellent yield with good selectivity.

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.

A novel method for preparing S-(perfluoroalkyl)-dibenzothiophenium trifluoromethanesulfonate

A method for preparing S-(perfluoroalkyl)-dibenzothiophenium trifluoromethanesulfonate shown as a general formula (I) by a one-pot process with significant effects is disclosed by the invention. The method includes reacting a biphenyl compound, perfluoroalkyl sulfonate, trifluoroacetic anhydride and trifluoromethanesulfonic acid. The biphenyl compound can be recovered and utilized so that the method is an environmentally friendly preparing method.

Industrial production method of 3,3',4,4'-tetrafluorobipheny

(The formula (I) is as shown in descriptions.) The invention relates to a high-yield production method of 3,3',4,4'-tetrafluorobipheny as shown in a formula (I). The compound is prepared by reacting 3,4-difluorophenyl magnesium halide with oxygen under the catalytic action of Mn(II) salt.

Hydroxytrifluoromethylation of Alkenes Using Fluoroform-Derived CuCF3

Hydroxytrifluoromethylation of alkenes using the fluoroform (CF3H)-derived [CuCF3] reagent is described. In the presence of additive B2Pin2 and air, this reagent effectively facilitates the addition of hydroxy and trifluoromethyl groups across an alkene double bond, a formal hydroxytrifluoromethylation process. Various β-trifluoromethyl alcohols can be synthesized from simple alkenes where the ultimate CF3 source is the industrial byproduct fluoroform.