454-87-5

Upstream product

• 98-16-8 3-trifluoromethylaniline 
• 109-63-7 boron trifluoride diethyl etherate 
• 7632-00-0 sodium nitrite 
• 106-40-1 4-bromo-aniline 

Downstream Products

• 401-80-9 3-fluoro-trifluoromethylbenzene 
• 199188-30-2 3-(trifluoromethyl)phenyl trifluoromethanesulfonate 
• 32578-33-9 3-(((trifluoromethyl)sulfonyl)oxy)benzoic acid 
• 51907-90-5 <(3-Trifluormethyl)phenyl>phosphonsaeure 
• 98-08-8 α,α,α-trifluorotoluene 
• 108864-09-1 (3-Trifluoromethyl-phenyl)trifluoroacetate 
• 1047641-44-0 4-anilino-3-benzoyl-5-phenyl-1-[3-(trifluoromethyl)phenyl]-1H-pyrazole 
• 1020074-00-3 C₁₈H₁₅F₃O₂ 
• 145439-14-1 4-(3-trifluoromethylphenyl)-furan-2(5H)-one 
• 1187180-17-1 3-benzoyl-1-(3-trifluoromethylphenyl)-5-methyl-4-(pyrrolidine-1-yl)-1H-pyrazole 
• 1187577-25-8 6,7-dimethoxy-3-(3-trifluoromethylbenzyl)-3,4-dihydro-1H-quinolin-2-one 
• 126309-76-0 1-(2-phenylethynyl)-3-(trifluoromethyl)benzene 
• 1231755-89-7 methyl (2E)-2-phenyl-3-(3-trifluoromethylphenyl)acrylate 
• 104201-66-3 trans-methyl 3-(3-(trifluoromethyl)phenyl)acrylate 

Relevant academic research and scientific papers

Aryl Diazonium Salts: Powerful Arylating Agents for Catellani-Typeortho-Arylation

The Catellani reaction provides an efficient synthetic approach to polyfunctionalized arenes. However, the selectiveortho-arylating reagents employed in these reactions have been strictly limited to activated bromoarenes. As demonstrated in this work, aryl diazonium salts bearing both electron-donating and electron-withdrawing substituents, after in situ transformations with KI into the corresponding iodoarenes, were efficient arylating reagents for Catellani typeortho-arylation approaches.

Aqueous and Visible-Light-Promoted C-H (Hetero)arylation of Uracil Derivatives with Diazoniums

Direct C5 (hetero)arylation of uracil and uridine substrates with (hetero)aryl diazonium salts under photoredox catalysis with blue light was reported. The coupling proceeds efficiently with diazonium salts and heterocycles in good functional group tolerance at room temperature in aqueous solution without transition-metal components. A plausible radical mechanism has been proposed.

Gold(I)-Catalyzed Cross-Coupling Reactions of Arenediazonium Salts with Alkynoic Acids

Abstract: The reaction of simple alkynoate salts with isolated arenediazonium tetrafluoroborate salts that had been pre-conditioned with the gold(I) catalyst AuCl(Me2S) led to the formation of cross-coupled products via a decarboxylative Sonogashira reaction process in modest yield and under mild conditions. The major by-product is a defunctionalized aryl moiety stemming from the diazonium salt, which competitively forms via hydrodediazonation. Good functional group tolerance and reaction site selectivity were attained in this limited investigation.

Dual palladium-photoredox catalyzed chemoselective C-H arylation of phenylureas

A highly chemoselective C-H arylation of phenylureas has been accomplished using dual palladium-photoredox catalysis at room temperature without any additives, base or external oxidants. Regioselective C-H arylation ofN,N'-diaryl substituted unsymmetrical phenylureas has also been accomplished by a careful choice of aryl groups.

Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature

A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d-glucal, d-galactal, l-rhamnal, d-xylal and d-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.

An unprecedentedly simple method of synthesis of aryl azides and 3-hydroxytriazenes

Fischer's approach towards the synthesis of aryl azides and triazinoles from diazonium salts and hydroxylammonium chloride (phenylhydraxylamine) was reinvestigated and optimized. The new methodology enables the preparation of aryl azides and triazinoles in high yields in water at room temperature. The procedure is very simple, robust, easily scalable, reproducible, and "green".

Pyridine-promoted dediazoniation of aryldiazonium tetrafluoroborates: Application to the synthesis of SF5-substituted phenylboronic esters and iodobenzenes

Pyridine promotes dediazoniation of aryldiazonium tetrafluoroborates. The formed aryl radicals were trapped with B2pin2, iodine, or tetrahydrofuran to afford boronic esters, iodobenzenes and benzenes, respectively. The application to the synthesis of (pentafluorosulfanyl) phenylboronic esters, iodo(pentafluorosulfanyl)benzenes and (pentafluorosulfanyl)benzene is shown.

A family of low molecular-weight, organic catalysts for reductive C-C bond formation

Hydrazines form a new family of low molecular-weight reducing agents for diazonium salts. Using only small amounts of hydrazine catalyst, the coupling of diazonium salts to a variety of reactive partners has been achieved, without the requirement for either metal adjuvants or irradiation with visible or ultraviolet light. The generality of the concept proposed herein as well as its advantages in the preparative scale is outlined and discussed.

Diazonium exchange and migration of pivaloyl group upon azo coupling of β-enaminones

4,4-Dimethyl-1-methylamino-1-phenyl-2-(substituted phenyldiazenyl)pent-1- en-3-ones (prepared upon azo coupling of 4,4-dimethyl-1-methylamino-1- phenylpent-1-en-3-one 6a with the corresponding benzenediazonium tetrafluoroborates) react with another molecule of substituted benzenediazonium tetrafluoroborate (in dichloromethane in the presence of anhydrous sodium acetate) to form substituted 4,4-bis(substituted phenyldiazenyl) derivatives 8. The second azo coupling is reversible. Derivatives 8 undergo either reverse cleavage of a diazonium ion or [1,3] sigmatropic rearrangement forming substituted formazane 9. In the case of the sequential use of two different diazonium tetrafluoroborates, the less electrophilic group splits off more easily. The structures of the products 9 were studied by means of X-ray, 1H, 13C, 19F and 15N NMR and MALDI HRMS analyses. The formazans 9 exhibit a reduced mobility of the phenyl group adjacent to the pivaloyl group, giving rise to anisochronism of proton and carbon atoms, to eventually form conformers. The reduced mobility was observed by means of NMR spectroscopy. A temperature dependence of the spectral behaviour was also studied. 4,4-Dimethyl-1-methylamino-1-phenyl-2-(substituted phenyldiazenyl)pent-1-en-3-ones react with benzenediazonium tetrafluoroborates through ipso attack, the products of which can undergo either migration of the pivaloyl group to form acylated formazans or reverse reaction to give the products of single azo coupling. With different diazonium salts an exchange of phenyldiazenyl groups is observed. Copyright

One-pot fluoro-de-diazoniation of anilines in organic medium

Treatment of anilines with tert-butyl nitrite in the presence of boron trifluoride in ortho-dichlorobenzene leads to in situ fluoro-de-diazoniation and affords the corresponding fluoroaromatics with fair yields. This process, conducted in organic medium without Broensted acids, does not require isolation of hazardous diazonium salts and reduces the amounts of wastes. The results of the first screening are given.