A simple, broadly applicable protocol for amidation and esterification reactions is described. Thereby, 4-acetamidophenyl triflimide (AITF), a crystalline stable reagent, is employed for the activation of carboxylic acids. The use of AITF as a coupling agent is demonstrated in the synthesis of peptides, amides and esters under mild conditions in good to excellent yields. Notably, peptide segment condensations were also accomplished. A diverse array of synthetic protocols showcasing a broad substrate scope and good functional group compatibility were accomplished. Herein, we systematically summarized the use of AITF in peptide synthesis strategies.