1983-22-8

Upstream product

• 82203-90-5 α-(trifluoroacetyl)-p-nitrobenzylidenetriphenylphosphorane 
• 94837-99-7 1-[2-chloro-3,3,3-trifluoro-1-propenyl]-4-nitrobenzene 
• 636-98-6 p-nitrobenzene iodide 
• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 2767-70-6 (p-nitrobenzyl)triphenylphosphonium bromide 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 34091-69-5 (2-chloro-3,3,3-trifluoroprop-1-en-1-yl)benzene 
• 103654-96-2 1-(α,α-dichloro-β,β,β-trifluoroethyl)benzylalcohol 
• 937-31-5 (4-Nitrophenyl)acetylene 
• 129946-88-9 Umemoto's reagent 

Downstream Products

• 122247-13-6 3-(2,6-Dichloro-phenyl)-4-(4-nitro-phenyl)-5-trifluoromethyl-isoxazole 
• 122247-06-7 3-(2,6-Dichloro-phenyl)-5-(4-nitro-phenyl)-4-trifluoromethyl-isoxazole 
• 141543-57-9 1-(2,6-Dichloro-phenyl)-4-(4-nitro-phenyl)-5-trifluoromethyl-1H-[1,2,3]triazole 
• 141543-49-9 1-(2,6-Dichloro-phenyl)-5-(4-nitro-phenyl)-4-trifluoromethyl-1H-[1,2,3]triazole 
• 877458-04-3 Bu₃SnC(CF₃)C(CCCF₃)C₆H₄-NO₂-p 
• 1147879-78-4 C₁₅H₂₀F₃NO₂Si 
• 1147879-93-3 C₁₅H₂₀F₃NO₂Si 
• 1187747-18-7 (Z)-1-(3,3,3-trifluoro-1-(4-nitrophenyl)prop-1-en-2-yl)pyrrolidine 
• 1148050-15-0 1-[(1Z)-2-tert-butoxy-3,3,3-trifluoroprop-1-enyl]-4-nitrobenzene 

Relevant academic research and scientific papers

SYNTHESIS OF ARYLTRIFLUOROMETHYLACETYLENES

Aryltrifluoromethylacetylenes were synthesized by an intramolecular Wittig reaction of trifluoroacetylarylidenephosphoranes, which were synthesized from arylmethyl halides.

Diverse copper(iii) trifluoromethyl complexes with mono-, bi- and tridentate ligands and their versatile reactivity

Cu(iii) trifluoromethyl complexes are proposed as essential intermediates for many copper-promoted trifluoromethylation reactions, but remain elusive and scarcely explored. We report herein the isolation and spectroscopic and X-ray crystallographic charac

Cu-promoted oxidative trifluoromethylation of terminal alkynes with difluoromethylene phosphobetaine

Difluoromethylene phosphobetaine (Ph3P+CF 2CO2-, PDFA), a known difluorocarbene reagent, was found to be able to efficiently trifluoromethylate terminal alkynes in the presence of Cu(I) and potassium fluoride. The transformation proceeded smoothly to afford the corresponding trifluoromethylated acetylenes in moderate yields. A difluorocarbene precursor, difluoromethylene phosphobetaine (Ph 3P+CF2CO2-, PDFA) was found to be able to act as a trifluoromethylating reagent in the presence of fluoride. The oxidative trifluoromethylation of terminal alkynes with PDFA promoted by Cu(I) occurred smoothly to give the corresponding trifluoromethylated acetylenes in moderate yields. Copyright

Copper-catalyzed trifluoromethylation of terminal alkynes using Umemoto's reagent

A copper-catalyzed method for trifluoromethylation of terminal alkynes with Umemoto's reagent has been developed. The reaction is conducted at room temperature and shows good tolerance to a variety of functional groups.

Synthetic approach to alkoxy-β-(trifluoromethyl)styrenes and their application in the synthesis of new trifluoromethylated heterocycles

A new convenient stereoselective pathway to alkoxy-β-(trifluoromethyl) styrenes is described. Reactions of β-chloro- and β-bromo-β- (trifluoromethyl)styrenes with sodium methoxide and potassium tert-butoxide led to methoxy- and tert-butoxy-β-(trifluoromethyl) styrenes in good to excellent yields. Bromination of tert-butoxy-β-(trifluoromethyl)styrenes proceeded with formation of aryl(bromo)methyl trifluoromethyl ketones. The latter compounds were found to be useful starting materials for the synthesis of different heterocyclic compounds bearing a trifluoromethyl group. In this way trifluoromethylated derivatives of imidazopyridine, imidazopyrimidine, imidazobenzimidazole, imidazothiazole, thiazole, and aminothiazole were obtained in moderate to high yield. Georg Thieme Verlag Stuttgart.

Facile syntheses of various per- or polyfluoroalkylated internal acetylene derivatives

Treatment of per- or polyfluoroalkylated vinyl iodides 5 with 2equiv. of n-BuLi in THF produced the corresponding lithium acetylides in situ, which were transformed into zinc acetylides by the addition of ZnCl2· TMEDA complex into the reaction mixture. The in situ generated zinc acetylides were exposed to the cross-coupling conditions such as ArI/cat. Pd(PPh 3)4, reflux, 6-12 h, giving rise to the desired per- or polyfluoroalkylated acetylenes in high yields. In the case of trifluoromethylated acetylene, commercially available 2-bromo-3,3,3-trifluoropropene 6 could also be used instead of 5 as the starting material. In the acetylenes having a fluoroalkyl group and an aliphatic side chain, vinyl iodides 7, prepared by radical addition of perfluoroalkyl iodide to terminal acetylenes, were treated with t-BuOK at room temperature or at the reflux temperature of benzene, affording the desired compounds in good yields.

Synthesis of 1-Aryl-3,3,3-trifluoro-1-propynes and 3,5-Diaryl-4-trifluoromethylisoxazoles

Diaryl-substituted trifluoromethylisoxazoles 5a-i, 6a-c, and 6e-i are synthesized from aromatic nitrile oxides and various substituted 1-aryl-3,3,3-trifluoro-1-propynes.

Studies on Organic Fluorine Compounds. XLII. Synthesis and Reactions of Phenyltrifluoromethylacetylenes

Phenyltrifluoromethylacetylene (4a) was synthesized by the pyrolysis of triphenylphosphonium α-(trifluoroacetyl)benzylide (3a), which was easily derived from benzyl halide (1a).This method can be used for the synthesis of 4-substituted-phenyltrifluoromethylacetylenes (4).The 1,3-dipolar reaction of 4 with diazomethane and phenyl azide proceeds readily to give trifluoromethylated pyrazoles and triazoles.Keywords - trifluoromethyl; acetylene; 1,3-dipolar reaction; intramolecular Wittig reaction; trifluoroacetylphosphonium ylide; pyrazole; diazomethane; phenyl azide