Reaction of secondary amides with diethylaminosulphur trifluoride

Monofluorination of Organic Compounds: 10 Years of Innovation

“…No new methods for the preparation of imidoyl fluorides have been published recently. As such, they are still generally prepared by the reaction of secondary amides with DAST 553 or by the nucleophilic fluorination of imidoyl bromides or chlorides. 554 3.2.6.…”

Synthesis of Carbamoyl Fluorides via a Selective Fluorinative Beckmann Fragmentation

“…Next, we explored the reactivity of non- N -substituted isatin-3-oxime 11 under the given reaction conditions (Scheme a). Although the secondary amide and oxime functionalities of substrate 11 were presumed to compete as both are nucleophilic, the oxime was found to have complete selectivity in the reaction with DAST. Interestingly, 0.5 equiv of DAST was sufficient to fully consume 11 , and a major product was identified as urea 14a (38% isolated yield).…”

Fluorinative α-cleavage of cyclic ketoximes with diethylaminosulfur trifluoride: an efficient synthesis of fluorinated carbonitriles

“…1 Since diethylaminosulfur trifluoride (DAST), a reagent converting aliphatic alcohols into alkyl fluorides, has been introduced into organic synthesis, 2 there have been several reports concerning new fluorinating methods. [3][4][5][6][7][8][9] Among the methods, we reported the reaction of DAST with tertiary cyclopropyl silyl ethers causing ring opening to give allylic fluorides. 10 Here we describe a novel reaction involving the treatment of cyclic ketoximes 1 with DAST to cause a ring fragmentation resulting in the formation of fluorinated carbonitriles 2.…”