An N-Fluorinated Imide for Practical Catalytic Imidations

Abstract

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.