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An N -Fluorinated Imide for Practical Catalytic Imidations.

Yuno OeRyuhei YoshidaAiri TanakaAkiya AdachiYuichiro IshibashiTakashi OkazoeKohsuke AikawaTakuya Hashimoto
Published in: Journal of the American Chemical Society (2022)
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.
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