A New Method of Perfluoroalkylation

Syntheses and lipophilicity measurement of Nα/N-terminus-1,1-dihydroperfluoroalkylated α-amino acids and small peptides

“…Preparation of (1,1-dihydroperfluoroalkyl)phenyliodonium N,Nbis(trifluoromethylsulfonyl)imides Perfluoroalkyl aryliodonium salts were first synthesized by Yagupolskii et al in the late 1970's [23]. In the early 1980's, Umemoto and Gotoh [24] synthesized perfluoroalkyl and 1,1-dihydroperfluoroalkyl aryliodonium triflates including (2,2,2-trifluoroethyl)phenyl iodonium triflate, which was later prepared using the modified method by Resnati [25] and used for N-trifluoroethylation of amino alcohols under dry conditions.…”

Strategies for nucleophilic, electrophilic, and radical trifluoromethylations

“…It has to be noted that iodonium salts including ptolylperfluoroalkyliodonium chlorides, perfluoroalkylphenyliodonium triflates (FITS) and perfluoroalkylphenyliodonium hydrogensulfates (FIS), which were described by Umemoto, have been reported as perfluoroalkylating agents but not as trifluoromethylating agents [112][113][114]. The reason for that is because their synthetic intermediates have low stability compared to the intermediates having R f groups with more than one carbon atom [92].…”

Novel 10‐I‐3 Hypervalent Iodine‐Based Compounds for Electrophilic Trifluoromethylation

“…They argued that the weak CF 3 ÀI bond might be cleaved in this condensation step. For this reason we chose to follow a nucleophilic ligand displacement strategy instead of Yagupolskiis [24] and Umemotos condensation approach. An alternative electrophilic source of the trifluoromethyl group based on hypervalent iodine is a desirable target because of relatively cheap starting materials and the potential opportunity to recycle the iodine-containing reduced species after the delivery of the CF 3 fragment.…”