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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
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Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
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Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
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One of the common methods to prepare nitriles is the dehydration of amides. This method requires strong dehydrating agents like phosphorous pentoxide or boiling acetic anhydride for converting amides to nitriles. Another reagent namely, thionyl chloride also accomplishes the dehydration of amides, where amide acts as a nucleophile. The first step of the mechanism involves the nucleophilic attack by the amide on the thionyl chloride to form an intermediate. In the next step, the electron pairs...
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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.

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|January 27, 2022
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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.

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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.