N-Fluoroalkylanilines and Their N-Hydroxyalkyl Derivatives

The first example of linear peptides containing a N-trifluoroethylated backbone amide linkage and the surprising solution dynamics observed by 19F NMR

“…Based on Dickey's research [12], trifluoroethylation of anilines with 2-chloro-1,1,1-trifluoroethane by autoclave reactions, and Hansen's work [13], trifluoroethylation of diethylamine with trifluoroethyl trifluoromethanesulfonate (triflate), Steinman et al [2] prepared and used triclate to obtain the secondary Ntrifluoroethylated anilines and aminobenzophenones. These were then coupled directly with bromoacetyl bromide and phthalimidoacetyl chloride to form desired tertiary amide functionalities.…”

Iron porphyrin-catalyzed N-trifluoroethylation of anilines with 2,2,2-trifluoroethylamine hydrochloride in aqueous solution

“…[1][2][3] N-triuoroethylated amines are widely used as platform chemicals in the elds of synthetic organic, medicinal and agrochemistry. [4][5][6] To obtain N-tri-uoroethylated amines, two approaches have been used: (1) using aryl halides via the reaction with 2,2,2-triuoroethylamine [8][9][10] and (2) using amines through the reaction with tri-uoroethylated reagents such as triuoroethyl chloride, 11 hypervalent-iodine-CH 2 CF 3 reagents, 12 triuoroacetic acid 13 and uoroalcohols. 7 Triuorodiazoethane (CF 3 CHN 2 ) synthesized from triuoroethylamine hydrochloride was widely used as an attractive CF 3 -containing synthon, largely owing to the pioneering work in 1943 from Gilman and Jones.…”

ChemInform Abstract: Silver(I)‐Catalyzed N‐Trifluoroethylation of Anilines and O‐Trifluoroethylation of Amides with 2,2,2‐Trifluorodiazoethane.

“…[6] In 1986, Umemoto and co-workers reported am ethod to achieve N-trifluoroethylation by using ah ypervalent-iodine-CH 2 CF 3 reagent. [6] In 1986, Umemoto and co-workers reported am ethod to achieve N-trifluoroethylation by using ah ypervalent-iodine-CH 2 CF 3 reagent.…”

“…[12] Subsequently,w ei nvestigated the N-trifluoroethylation of ethyl 4-aminobenzoate (1a)w ith the stock toluene solution of CF 3 6 ,a nd AgSbF 6 were found to be effective,thus affording the desired product 2ain moderate to good yields.Among these salts,A gSbF 6 turned out to be the best catalyst for the reaction (entry 5). [12] Subsequently,w ei nvestigated the N-trifluoroethylation of ethyl 4-aminobenzoate (1a)w ith the stock toluene solution of CF 3 6 ,a nd AgSbF 6 were found to be effective,thus affording the desired product 2ain moderate to good yields.Among these salts,A gSbF 6 turned out to be the best catalyst for the reaction (entry 5).…”

“…At the outset, aC F 3 CHN 2 solution in toluene was prepared from commercially available CF 3 CH 2 NH 2 ·HCl, according to the method reported by Carreira and coworkers. [12] Subsequently,w ei nvestigated the N-trifluoroethylation of ethyl 4-aminobenzoate (1a)w ith the stock toluene solution of CF 3 6 ,a nd AgSbF 6 were found to be effective,thus affording the desired product 2ain moderate to good yields.Among these salts,A gSbF 6 turned out to be the best catalyst for the reaction (entry 5). Thee ffect of solvent was then investigated (entries 9-14), and toluene,C H 2 Cl 2 , Scheme 1.…”