A third generation of radical fluorinating agents based on N-fluoro-N-arylsulfonamides was written by Meyer, Daniel;Jangra, Harish;Walther, Fabian;Zipse, Hendrik;Renaud, Philippe. And the article was included in Nature Communications in 2018.Safety of N-Isopropylbenzenesulfonamide This article mentions the following:
The preparation, use and properties of N-fluoro-N-arylsulfonamides (NFASs), a class of fluorinating reagents suitable for radical fluorination under mild conditions was reported. Their N-F bond dissociation energies (BDE) are 30-45 kJ mol-1 lower than the N-F BDE of the reagents of the second generation. This favored clean radical fluorination processes over undesired side reactions. The utility of NFASs was demonstrated by a metal-free radical hydrofluorination of alkenes including an efficient remote C-H fluorination via a 1,5-hydrogen atom transfer. NFASs have the potential to become the reagents of choice in many radical fluorination processes. In the experiment, the researchers used many compounds, for example, N-Isopropylbenzenesulfonamide (cas: 5339-69-5Safety of N-Isopropylbenzenesulfonamide).
N-Isopropylbenzenesulfonamide (cas: 5339-69-5) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors. Amides are not in general accessible by the direct condensation of amines with carboxylic acids for two reasons: first, both components are readily deactivated by a transfer of a proton from the acid to the amine and second, the hydroxy unit on the carbonyl of the acid is a relatively poor leaving group. Nevertheless, the formation of five- and six-membered rings is often surprisingly simple provided that other factors can be brought into play to assist in the condensation.Safety of N-Isopropylbenzenesulfonamide
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics