An <i>N</i>-Fluorinated Imide for Practical Catalytic Imidations
Yuno Oe, Ryuhei Yoshida, Airi Tanaka, Akiya Adachi, Yuichiro Ishibashi, Takashi Okazoe, Kohsuke Aikawa, Takuya Hashimoto
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.