149054-29-5

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• 2070902-77-9 trifluoromethyl 4-fluorobenzene-1-sulfonate 
• 1197209-28-1 trifluoromethyl 4-methoxybenzenesulfonate 
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• 175676-42-3 trifluoromethyl 4-methylbenzenesulfonate 
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• 329685-40-7 4,4,5,5-tetramethyl-2-(3-phenylpropyl)-[1,3,2]dioxaborolane 
• 143583-08-8 O-(3-phenylpropyl)-S-methyl dithiocarbonate 
• 143583-03-3 3-[difluoro(methylthio)methoxy]-1-phenylpropane 

Relevant academic research and scientific papers

A Series of Deoxyfluorination Reagents Featuring OCF2Functional Groups

Research on perfluoroalkyl ether carboxylic acids (PFECAs) as alternatives for perfluoroalkyl substances continues with the goal of protecting the environment. However, very little is known about the utilization of decomposition products of PFECAs. We report herein a new series of deoxyfluorination reagents featuring OCF2 functional groups derived from certain PFECAs. Alkyl fluorides were generated from various alcohols in ≤97% yield by these novel reagents. The mechanistic experiment verified in situ generation of carbonic difluoride (COF2).

Silver-Catalyzed Trifluoromethoxylation of Alkyl Trifluoroborates

A silver-catalyzed trifluoromethoxylation of alkyl trifluoroborates with trifluoromethyl arylsulfonate as the trifluoromethoxylation reagent has been reported for the first time. This reaction is performed under mild reaction conditions and has wide functional group compatibility. In addition, the mechanism of this site-specific trifluoromethoxylation is proposed as a radical pathway.

Synthesis of Chloro(phenyl)trifluoromethyliodane and Catalyst-Free Electrophilic Trifluoromethylations

The present work deals with a challenge in the synthesis of aryltrifluoromethyliodanes (ArICF3X) and develops a direct route to PhICF3Cl via a simple ligand-exchange reaction of PhI(OCOCF3)2, Me3SiCF3, and NaCl for the first time. The I-Cl bond length in PhICF3Cl supports its iodonium character, which enables an enhanced CF3-transfer capability in electrophilic S-, O-, N-, and C-trifluoromethylations as well as in catalyst-free trifluoromethylation-cyclizations of arylisonitriles.

Synthesis of trifluoromethyl ethers and difluoro(methylthio)methyl ethers by the reaction of dithiocarbonates with IF5-pyridine-HF

Trifluoromethyl ether and difluoro(methylthio)methyl ether of phenols and aliphatic alcohols were selectively synthesized from the corresponding dithiocarbonates. When IF5-pyridine-HF was used alone in the reaction of the dithiocarbonate, the difluoro(methylthio)methyl ether was selectively formed. On the other hand, by the additional use of Et3N-6HF with IF5-pyridine-HF, trifluoromethyl ether was formed selectively. Various functional groups such as ester, ether, amide, and acetonide could tolerate the reaction conditions, and various functionalized difluoro(methylthio)methyl ethers and trifluoromethyl ethers were synthesized.

METHOD FOR PRODUCING FLUORINATED ORGANIC COMPOUND AND FLUORINATING REAGENT

Object: An object of the present invention is to provide a method for producing, with a high yield, a fluorinated organic compound, the fluorinated organic compound having not been produced with a sufficient yield by a conventional method for producing a fluorinated organic compound using a fluorinating agent containing IF5-pyridine-HF alone. Another object of the present invention is to provide a fluorinating reagent. Means for achieving the object: A method for producing a fluorinated organic compound comprising step A of fluorinating an organic compound by bringing the organic compound into contact with (1) IF5-pyridine-HF and (2) at least one additive selected from the group consisting of amine hydrogen fluorides, XaF (wherein Xa represents hydrogen, potassium, sodium, or lithium), oxidizers, and reducing agents.

A convenient synthesis of trifluoromethyl ethers by oxidative desulfurization-fluorination of dithiocarbonates

Trifluoromethyl ethers R-OCF3 are easily synthesized from the corresponding dithiocarbonates R-OCS2Me (R = aryl or primary alkyl) by a reagent system consisting of 70% HF/pyridine and an N-halo imide. When the reaction is applied to R-OCS2Me wherein R = secondary alkyl, tertiary alkyl, or benzylic group, fluorination leading to the corresponding alkyl fluorides R-F is achieved, whereas a combination of 50% HF/pyridine and N- bromosuccinimide affords the corresponding trifluoromethyl ethers R-OCF3 (R = secondary).

Oxidative desulfurization-fluorination of xanthates. A convenient synthesis of trifluoromethyl ethers and difluoro (methylthio)methyl ethers

Treatment of xanthates R-OC(S)SMe with (HF)9/Py and 1,3-dibromo-5,5-dimethylhydantoin gives trifluoromethyl ethers R-OCF3 through intermediates R-OCF2SMe, which could be isolated upon treatment of xanthates with n-Bu4N+H2F3- and N-bromosuccinimide.