Triflamides and Triflimides: Synthesis and Applications

Abstract

Among the variety of sulfonamides, triflamides (CF3SO2NHR, TfNHR) occupy a special position in organic chemistry. Triflamides are widely used as reagents, efficient catalysts or additives in numerous reactions. The reasons for the widespread use of these compounds are their high NH-acidity, lipophilicity, catalytic activity and specific chemical properties. Their strong electron-withdrawing properties and low nucleophilicity, combined with their high NH-acidity, makes it possible to use triflamides in a vast variety of organic reactions. This review is devoted to the synthesis and use of N-trifluoromethanesulfonyl derivatives in organic chemistry, medicine, biochemistry, catalysis and agriculture. Part of the work is a review of areas and examples of the use of bis(trifluoromethanesulfonyl)imide (triflimide, (CF3SO2)2NH, Tf2NH). Being one of the strongest NH-acids, triflimide, and especially its salts, are widely used as catalysts in cycloaddition reactions, Friedel–Crafts reactions, condensation reactions, heterocyclization and many others. Triflamides act as a source of nitrogen in C-amination (sulfonamidation) reactions, the products of which are useful building blocks in organic synthesis, catalysts and ligands in metal complex catalysis, and have found applications in medicine. The addition reactions of triflamide in the presence of oxidizing agents to alkenes and dienes are considered separately.

Suspect, Nontarget Screening, and Toxicity Prediction of Per- and Polyfluoroalkyl Substances in the Landfill Leachate

“…The HNTf2, a polyfluorinated sulfonimide dimer, is widely used as a catalyst in organic synthesis . It was reported in surface water in Beijing (China) .…”

Chemical emasculation in cowpea (Vigna unguiculata (L.) Walp.) and dicotyledonous model species using trifluoromethanesulfonamide (TFMSA)

“…Most of the CHAs belong to plant hormone groups, including auxins and auxin inhibitors, gibberellins and ethylene; they are toxic to the female structures or F 1 seeds, and have a narrow window of timing for application (Colombo and Galmarini 2017 ). TFMSA is a common chemical and not yet found to be a plant hormone (Loussaert 2004 ; Moskalik and Astakhova 2022 ; Shainyan and Tolstikova 2013 ). TFMSA is classified as GHS system with code H315 + H320 ( https://pubchem.ncbi.nlm.nih.gov/ghs/#_prec ).…”

“…9, 2021 ) are classified as combined code with H315 + H320 indicates skin and eye irritation ( https://pubchem.ncbi.nlm.nih.gov/compound/79001 ). Trifluoromethanesulfonamide (TFMSA) is a common chemical and not yet found to be a plant hormone (Loussaert 2004 ; Moskalik and Astakhova 2022 ; Shainyan and Tolstikova 2013 ). TFMSA has been studied as a male sterility-specific CHA with potential applications in maize (Loussaert 2004 ) and sorghum (Hodnett and Rooney 2018 ).…”

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

“…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].…”