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An N-Fluorinated Imide for Practical Catalytic Imidations
Yuno Oe1, Ryuhei Yoshida1, Airi Tanaka1
1Chiba Iodine Resource Innovation Center and Department of Chemistry, Graduate School of Science, Chiba University, 1-33, Yayoi, Inage, Chiba 263-8522, Japan.
A novel N-fluorinated imide, N-fluoro-N-(fluorosulfonyl)carbamate (NFC), enables efficient oxidative C-N bond formation. This reagent overcomes limitations of previous methods, offering a versatile handle for synthesizing amines and related compounds.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- Catalytic imidation is crucial for oxidative carbon-nitrogen bond formation.
- Existing methods using N-fluorobenzenesulfonimide (NFSI) incorporate an undesirable moiety, limiting synthetic utility.
Purpose of the Study:
- To develop a novel N-fluorinated imide reagent for improved oxidative C-N bond formation.
- To demonstrate the versatility of the new reagent as a synthetic handle for derivatization.
Main Methods:
- Synthesis of N-fluoro-N-(fluorosulfonyl)carbamate (NFC).
- Copper-catalyzed imidation of benzene derivatives using NFC.
- Imidocyanation of aliphatic alkenes using NFC.
Main Results:
- NFC serves as a modular synthetic handle, allowing one-step derivatization to amines, sulfonamides, and sulfamides.
- NFC exhibits superior reactivity compared to NFSI in copper-catalyzed imidation and imidocyanation reactions.
- The attached imide moiety in NFC is easily transformed, enhancing its synthetic value.
Conclusions:
- NFC is a highly effective reagent for oxidative C-N bond formation.
- The developed method overcomes the limitations associated with NFSI-mediated reactions.
- NFC offers a versatile and valuable tool for organic synthesis.
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