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Preparation of Amides01:29

Preparation of Amides

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Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
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Peptide Bonds

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A peptide bond covalently attaches amino acids through a dehydration reaction. One amino acid's carboxyl group and another amino acid's amino group combine, releasing a water molecule. The resulting bond is the peptide bond. The products that such linkages form are peptides. As more amino acids join this growing chain, the resulting chain is a polypeptide. Each polypeptide has a free amino group at one end. This end has the N-terminal, or the amino-terminal, and the other end has a free...
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Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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α-Hydroxy Ketones via Reductive Coupling of Esters: Acyloin Condensation Overview01:19

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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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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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CITU: A Peptide and Decarboxylative Coupling Reagent.

Justine N deGruyter1, Lara R Malins1, Laurin Wimmer1

  • 1Department of Chemistry, The Scripps Research Institute , 10550 North Torrey Pines Road, La Jolla, California 92037, United States.

Organic Letters
|November 9, 2017
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Tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (CITU) is a safe, economical reagent for acylation and decarboxylative cross-coupling. It offers improved yields and simplified procedures in chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Reagent Development

Background:

  • Acylation and decarboxylative cross-coupling are fundamental transformations in organic synthesis.
  • Existing reagents often present safety concerns or high costs.
  • There is a need for more efficient and economical coupling reagents.

Purpose of the Study:

  • To introduce Tetrachloro-N-hydroxyphthalimide tetramethyluronium hexafluorophosphate (CITU) as a novel reagent.
  • To evaluate CITU's efficacy in acylation reactions.
  • To assess CITU's utility in decarboxylative cross-coupling reactions.

Main Methods:

  • Synthesis and characterization of CITU.
  • Application of CITU in various acylation reactions.
  • Utilizing CITU in a range of decarboxylative cross-coupling transformations.

Main Results:

  • CITU demonstrates comparable reactivity to common coupling reagents in acylation.
  • CITU offers enhanced safety and reduced cost compared to existing acylation reagents.
  • CITU enables increased yields, faster reaction times, and simplified procedures in decarboxylative couplings.

Conclusions:

  • CITU is a versatile and cost-effective reagent for both acylation and decarboxylative cross-coupling.
  • The use of CITU can lead to more efficient and safer synthetic protocols.
  • CITU represents a valuable addition to the toolkit of synthetic chemists.