Recent trends in the chemistry of triflamides

The Reactions of Alkenes with Phenyl-N-triflylimino-λ3-iodane: Solvent and Oxidant Impact

“…More stable than triflylimino-λ 3 -bromane are triflylimino-λ 3 -iodanes. The N-triflyl-substituted analogs of the latter, N-triflylimino-λ 3 -iodanes ArI=NTf, were synthesized by the reaction of iodosobenzenes ArI=O with triflamide as late as in 2022 and used for amidation or imidation of phosphines and 1,3-diketones [26].…”

“…N-Trifluoromethylsulfonyl (triflyl) substituted nitrogen compounds occupy a unique place in organic chemistry [1][2][3]. The triflyl group is a very strong electron-withdrawing substituent responsible for the high NH-acidity of triflamides, their specific catalytic activity, the ability to form strong intra-and intermolecular hydrogen bonds, and a number of specific chemical properties.…”

“…The triflyl group is a very strong electron-withdrawing substituent responsible for the high NH-acidity of triflamides, their specific catalytic activity, the ability to form strong intra-and intermolecular hydrogen bonds, and a number of specific chemical properties. Low nucleophilicity and high NH-acidity allow triflamides to be used in a variety of organic reactions [1][2][3].…”

“…One of the most efficient methods for the synthesis of N-triflylaziridines is the reaction of alkenes with N-triflylimino-λ 3 -bromane 4-CF3C6H4Br=NTf [20,21] prepared in situ or in advance through several steps [21,22] (Scheme 1, route 3). The reagent is formed by the reaction of triflamide with 4-CF3C6H4Br(OAc)2 synthesized, in turn, by treating difluoride 4-CF3C6H4BrF2 with acetic anhydride [21].…”