3360-62-1

Upstream product

• 3853-91-6 2,3,4,5,6-pentamethyliodobenzene 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 87-85-4 Hexamethylbenzene 
• 55642-42-7 bis(trifluoromethyl)tellurium 
• 2314-97-8 iodotrifluoromethane 
• 700-12-9 pentamethylbenzene, 
• 32913-08-9 pentamethylbenzenetricarbonylchromium⁽⁰⁾ 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 75-63-8 Bromotrifluoromethane 
• 1080-50-8 pentamethyl-trichloromethyl-benzene 

Relevant academic research and scientific papers

The first nucleophilic C-H perfluoroalkylation of aromatic compounds via (arene)tricarbonylchromium complexes

The first nucleophilic perfluoroalkylation of arenes is based on the arene π-system activation via (η6-arene)tricarbonylchromium complexes. Perfluoroalkyl anions generated from Me3SiRF and a fluoride ion source [Me4N]F exclusively attack the arene ligand under mild conditions. The formed negatively charged analogs of Meisenheimer adducts readily undergo a one-pot oxidation to perfluoroalkyl arenes.

Palladium-Catalyzed Trifluoromethylation of (Hetero)Arenes with CF3Br

The CF3 group is an omnipresent motif found in many pharmaceuticals, agrochemicals, catalysts, materials, and industrial chemicals. Despite well-established trifluoromethylation methodologies, the straightforward and selective introduction of such groups into (hetero)arenes using available and less expensive sources is still a major challenge. In this regard, the selective synthesis of various trifluoromethyl-substituted (hetero)arenes by palladium-catalyzed C-H functionalization is herein reported. This novel methodology proceeds under comparably mild reaction conditions with good regio- and chemoselectivity. As examples, trifluoromethylations of biologically important molecules, such as melatonin, theophylline, caffeine, and pentoxifylline, are showcased.

Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide

Trifluoromethylation of aromatic and hetero-aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide was investigated. Various trifluoromethylated benzene derivatives, six-membered nitrogen-containing aromatic compounds and five-membered hetero-aromatic compounds were obtained under mild conditions. General orientation of electrophilic substitution of aromatic compounds was observed similarly as reported in other radical trifluoromethylation previously.

TRIFLUORMETHYLIERUNGSREAKTIONEN VON Te(CF3)2 MIT HALOGENBENZOLEN UND METHYLBENZOLEN

Substituent effects on yields and regioselectivity of photochemical and thermal trifluoromethylation reactions of Te(CF3)2 with halogen benzenes and methyl benzenes are investigated under comparable conditions.All reactions lead to trifluoromethylated products.The yields of the thermal are always higher than those of the corresponding photochemical reactions.The reactivity of the halobenzenes increases in the series C6H5-F a sidereaction, but H-substitution is the primary reaction pathway.During the reactions with iodobenzene tellurium containing compounds are also formed.The reactions with methyl benzenes show an increase in reactivity in the series hexamethylbenzene mesitylene toluene p-xylene.In all cases only ring substituted products are detected.Reactions with toluene and p-xylene yield tellurium containing compounds as well as addition products.The 19F-n.m.r spectra of the products are given.

Sodium Perfluoroalkane Carboxylates as Sources of Perfluoroalkyl Groups

Sodium trifluoroacetate, in the presence of copper(I) iodide, is used as a source of trifluoromethyl to replace halogen by trifluoromethyl in benzenoid and heterocyclic aromatic systems, as well as in alkenyl and alkyl halogen compounds.The mechanism of this interesting copper-assisted process has been explored and an intermediate of the form - is proposed.Introduction of higher perfluoroalkyl groups from their respective sodium perfluoroalkane carboxylates has been demonstrated and the machanistic features are compared with those of the trifluoromethylation process.

Influence of Substituents on the Light-Induced Isomerization of the Homofulvene System: Photo-Isomerization of the Singlet Excited 1,2,3,5-Tetramethyl-4-methylene-endo- and -exo-6-(trifluoromethyl)bicyclohex-2-ene

Syntheses of the diastereomeric pairs 1,2,3,5-tetramethyl-4-methylene-endo- and -exo-6-(trifluoromethyl)bicyclohex-2-ene (endo-1d and exo-1d) as well as -endo-1d and -exo-1d are reported.Following singlet excitation both diastereomers are

Process for the preparation of aromatic trifluoromethyl compounds

A process for the preparation of an aromatic trifluoromethyl compound which comprises contacting an aromatic compound of the formula STR1 wherein R1 denotes hydrogen, alkyl, aryl, aralkyl, aryloxy, arylthio, polyhalogenoalkoxy or polyhalogenoalkylthio and the aromatic substituents R1 can in turn be substituted by halogen, alkyl, polyhalogenoalkyl, polyhalogenoalkoxy, polyhalogenoalkylthio, nitro, chlorocarbonyl or chlorosulfonyl, and R2, R3, R4 and R5 are independently hydrogen, halogen or alkyl and two adjacent radicals of the group R1 to R5 can conjointly form a three-membered to five-membered alkylene radical, with carbon tetrachloride and hydrogen fluoride at a temperature in the range of 50° C. to 140° C. Certain new aromatic trifluoromethyl compounds which can prepared by such a process are also disclosed.

COPPER(I) IODIDE ASSISTED REACTION OF NONACTIVATED IODOARENES WITH SODIUM TRIFLUOROACETATE IN HEXAMETHYLPHOSPHORIC TRIAMIDE. NUCLEAR TRIFLUOROMETHYLATION AND DIARYL ETHER FORMATION

Polymethyliodobenzenes react with sodium trifluoroacetate, in the presence of copper(I) iodide, in hexamethylphosphoric triamide at 150-180 deg C, giving a mixture of the corresponding polymethylbenzotrifluoride, parent hydrocarbon, and bis(polymethylphenyl) ether.