Catalytic
imidation using NFSI as the nitrogen source has become
an emerging tool for oxidative carbon–nitrogen bond formation.
However, the less than ideal benzenesulfonimide moiety is incorporated
into products, severely detracting its synthetic value. As a solution
to this challenge, we report herein the development of a novel N-fluorinated imide, N-fluoro-N-(fluorosulfonyl)carbamate (NFC), by which the attached imide
moiety acts as a modular synthetic handle for one-step derivatization
to amines, sulfonamides, and sulfamides. Furthermore, this study revealed
the superior reactivity of NFC as showcased in a copper-catalyzed
imidation of benzene derivatives and imidocyanation of aliphatic alkenes,
overcoming the limitation of NFSI-mediated reactions.
Efficient methods for the synthesis of fluorinated compounds have been intensively studied, recently. Development of practical fluorinating reagents is indispensable for this purpose. Herein, bench‐stable electrophilic fluorinating reagents were synthesized as N‐fluorobenzenesulfonimide (NFSI) substitutes. Reagents obtained by replacing one of the NFSI sulfonyl groups with an acyl group led to the highly selective monofluorination of silyl enol ethers with suppression of undesired overreaction, that is, difluorination. On the other hand, reagents bearing electron‐withdrawing substituents at NFSI benzenesulfonyl groups efficiently facilitated the difluorination of silyl enol ethers under base‐free conditions. Thus, both mono‐ and difluorinated target materials were prepared from the same substrate.
The palladium-catalyzed aminofluorination of styrenes using novel N-fluorobenzenesulfonimide (NFSI) derivatives with deprotectable substituents, and the selective deprotection and transformation of the resulting products into amines under the mild reaction conditions...
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.