1006904-69-3

Upstream product

• 178552-83-5 C₁₁H₁₁F₃O₅S 
• 1006904-71-7 2-(dimethylamino)-1,3-dimethylimidazolidin-2-ylium trifluoromethanolate 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 774-40-3 hydroxy-phenyl-acetic acid ethyl ester 
• 22065-57-2 ethyl 2-phenyldiazoacetate 
• 1006904-72-8 silver(I) trifluoromethoxide 
• 58929-02-5 ethyl 2,3-diphenyl-3-oxopropanoate 
• 3582-05-6 trifluoromethyl trifluoromethanesulfonate 

Relevant academic research and scientific papers

Quaternary Ammonium Trifluoromethoxide Salts as Stable Sources of Nucleophilic OCF3

The reaction of nucleophilic tertiary amines with trifluoromethyl and pentafluoroethyl methyl ethers provides quaternary ammonium trifluoromethoxide (NR4OCF3) and pentafluoroethoxide (NR4OCF2CF3) salts, respectively, in good yields. The new trifluoromethoxide salts disclosed herein are uniquely stable for extended periods of time in both the solid state and in solution, which complements contemporary reagents. Here we describe the preparation of a range of NR4OCF3 salts, their long-term stability, and utility in substitution reactions.

Facile Access to AgOCF3 and Its New Applications as a Reservoir for OCF2 for the Direct Synthesis of N?CF3, Aryl or Alkyl Carbamoyl Fluorides

The development of innovative fluorination strategies is greatly dependent also on the availability, safety and practicability of available fluorinating reagents. We herein show a straightforward and quantitative strategy for the preparation of valuable AgOCF3 at room temperature and showcase its performance in trifluoromethoxylations or as reservoir for O=CF2. This enabled the direct, practical and safe synthesis of valuable N-alkyl/aryl and N?CF3 carbamoyl fluorides from secondary amines and isothiocyanides, respectively. Our mechanistic data indicate that AgOCF3 does not liberate O=CF2 until it is activated by a nucleophilic co-reagent, reinforcing the stability of the salt under our new preparation strategy.

Silver-mediated direct trifluoromethoxylation of α-diazo esters: Via the -OCF3 anion

Silver-mediated direct trifluoromethoxylation of α-diazo esters and ketosteroid was disclosed. The reactions of alkyl α-diazo arylacetates with AgOCF3 or CF3SO2OCF3/AgF at -30 to 10 °C under a N2 atmosphere provided α-trifluoromethoxyl arylacetates in up to 90% yield, while alkyl α-diazo vinylacetates reacting with CF3SO2OCF3/AgF or AgOCF3 afforded γ-trifluoromethoxyl α,β-unsaturated esters in up to 94% yield. The α-diazo ketosteroid was also trifluoromethoxylated under the standard reaction conditions. This protocol allows for an effective and convenient access to a large number of synthetic building blocks, which are promising in the development of new functional OCF3-molecules.

Versatile application of trifluoromethyl triflate

Hydrolytically stable and easy to handle trifluoromethyl triflate was found to be a liquid reservoir of 'masked' difluorophosgene. Anhydrous F- sources cleave the S-O bond in trifluoromethyl triflate yielding quantitatively the trifluoromethanolate salts, being useful trifluoromethoxy group carriers. Reaction of trifluoromethanolates with in situ generated from o-trimethylsilylphenyl triflate benzyne leads to (trifluoromethoxy)benzene and fluorobenzene (ratio 85:15). Whereas an addition of trifluoromethanethiolate anion across a triple bond of benzyne leads to [(trifluoromethyl)sulfanyl]benzene solely.