Triflylpyridinium as Coupling Reagent for Rapid Amide and Ester Synthesis

Abstract

An effective method has been developed to facilitate the synthesis of amides and esters at ambient temperature within 5 min, in which a stable and easily accessible triflylpyridinium reagent is used. Remarkably, this method not only has a wide range of substrate compatibility but also could realize the scalable synthesis of peptide and ester via a continuous flow process. Moreover, excellent chirality retentions are presented during activation of carboxylic acid.

Visible-light-induced Fe(iii)-promoted reduction amidation of 1,4,2-dioxazol-5-one

“…Among the numerous synthetic avenues to amide, the most traditional and well-established approach revolves around the reaction of amine compounds, acting as nucleophiles, with carboxylic acids 5–8 or their derivatives. 9–12 Historically, the preparation of amides has encompassed a broad range of methods, including the employment of carbon diimide condensation reagents, 13–15 onium salt condensation reagents, 16–18 and organophosphorus condensation reagents. 19–21…”

AITF (4-acetamidophenyl triflimide) mediated synthesis of amides, peptides and esters

“…13 Recently, coupling reagents such as ynamides, 14 a,b allenones, 15 oxalyl chloride and triphenylphosphine oxide, 16 and 4,6-dichloro-5-nitropyrimidine (NDTP) 17 were reported for the synthesis of amides/peptides. Furthermore, methyltrimethoxysilane (MTM), 18 potassium hexafluorophosphate (KPF 6 ), 19 3,3-difluoro-1,2-diphenylcyclopropene (CpFluor), 20 pentafluoropyridine (PFP), 21 a,b propargyl sulfonium, 22 and triflylpyridinium 23 have also been delineated for direct amidation. Some of these methods generate by-products, require harsh conditions, involve the use of hazardous and expensive coupling reagents and produce large amounts of chemical wastes.…”