Synthesis and stability of strongly acidic benzamide derivatives

Abstract

Reactivity studies of strong organic acids based on the replacement of one or both of the oxygens in benzoic acids with the trifluoromethanesulfonamide group are reported. Novel derivatives of these types of acids were synthesized in good yields. The generated N-triflylbenzamides were further functionalized through cross-coupling and nucleophilic aromatic substitution reactions. All compounds were stable in dilute aqueous solutions. Studies of stability under acidic and basic conditions are also reported.

Keywords

• benzoic acid
• cross-coupling
• hydrolysis
• SNAr
• trifluoromethanesulfonamide