Bis(trifluoroacetoxy)iodo benzene (PIFA)-promoted transamidation of carboxamides and carboxylic acids with amines

Abstract

A simple and efficient method has been developed for the synthesis of amides promoted by PIFA [(bis(trifluoroacetoxy)iodo)benzene]. In this method, PIFA [(bis(trifluoroacetoxy)iodo)benzene] has been used as a useful promoter for the transamidation of dimethylformamide (DMF) with the amines. Besides, this hypervalent iodine smoothly promoted the N-formylation of various aromatic amines with formic acid. Notably, the small quantity of PIFA is found to be efficient for both strategies and large-scale synthesis can also be achieved. The present protocol involves a metal and solvent-free, mild, eco-friendly condition with a high yield of the amide products and moreover, the reactions are not air or moisture sensitive.

Phenyliodine bis(trifluoroacetate) as a sustainable reagent: exploring its significance in organic synthesis

“…Due to the paramount importance of the amide functionality, numerous synthetic strategies have evolved over time. Kamble et al 50 presented an effective, mild, metal-free procedure for catalyzing the transamidation reaction using PIFA (Scheme 1). High yields of amide analogs 3 were achieved by employing various aromatic amines 1, predominantly those featuring fluoro substituents.…”