Recent Advances in Transformation of Acyl Fluorides

Formation, Characterization, and Reactivity of Acyl Palladium Complexes in Pd(OAc)2/PCy3-Catalyzed Transformation of Acyl Fluorides

“…In the last decades, the utility of acyl fluorides has gained attention as an alternative carbon electrophile surrogate. They are easy-to-handle and suitably reactive synthetic materials among carboxylic acid derivatives that demonstrate moderate levels of electrophilicity and stability. , In the presence of appropriate transition-metal catalysts such as nickel or palladium, acyl fluorides function as an acyl, an aryl, or a fluorine , source, which imparts the potential to be utilized as not only a carbon electrophile, akin to other carboxylic acids, but also as a stable organic fluorination reagent. This type of utility has resulted in rapid development of transition metal-catalyzed transformations of acyl fluorides in recent years.…”

Ni-catalysed deamidative fluorination of amides with electrophilic fluorinating reagents

“…upon subjection to nucleophiles. 6,7 Moreover, acyl fluorides usually show improved reactivity and better selectivity than acyl chlorides not only in the acylation but also in various metal catalysed cross-coupling reactions. 8 The synthesis of acyl fluorides from amides with safe fluorinating reagents is interesting since it can provide new opportunities for further transformation of inert amides to other elaborate compounds.…”

Gram-Scale Preparation of Acyl Fluorides and Their Reactions with Hindered Nucleophiles

“…1 Although studied for more than a century, 2 they have recently found numerous applications in the synthesis of peptides, 1a esters, 3 amides, 4 acylphosphonates, 5 and as valuable substrates for transition-metal-catalyzed transformations. 1` c d , 6 Early methods for their preparation 7 were based mainly on the halogen exchange of acyl halides using inorganic salts such as KHF 2 , 8 spray-dried KF, 9 KF/TEBA, 10 NaF, 11 or CaF 2 -KF, 12 which had many limitations including the need for tedious drying, prolonged reaction times at high temperatures, and isolation of products by fractional distillation. 13 In turn methods developed in last few years utilize more sophisticated reagents designed for direct conversion of carboxylic acids under mild conditions.…”