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Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

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...
Preparation of Amides01:29

Preparation of Amides

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...
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview01:16

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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.
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...

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An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
06:19

An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis

Published on: November 22, 2024

Novel proton acceptor immonium-type coupling reagents: application in solution and solid-phase peptide synthesis.

Ayman El-Faham1, Fernando Albericio

  • 1Institute for Research in Biomedicine, Barcelona Science Park, Josep Samitier 1, 08028-Barcelona, Spain. aymanel_faham@hotmail.com

Organic Letters
|September 29, 2007
PubMed
Summary

A new proton acceptor coupling reagent improves solubility and coupling yields while reducing racemization. This novel reagent allows for the use of only one equivalent of base in chemical reactions.

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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center

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An Inexpensive Adaptation of a Commercial Microwave Reactor for Solid Phase Peptide Synthesis
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Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles (PPAs) and Related Biomaterials
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Constructing Cyclic Peptides Using an On-Tether Sulfonium Center
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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Coupling reagents are essential in organic synthesis.
  • Existing reagents face challenges with solubility and efficiency.
  • Minimizing racemization is crucial for stereoselective synthesis.

Purpose of the Study:

  • To introduce a novel proton acceptor coupling reagent.
  • To evaluate its performance compared to existing reagents.
  • To demonstrate its advantages in terms of solubility, yield, and stereoselectivity.

Main Methods:

  • Synthesis of the novel proton acceptor coupling reagent.
  • Evaluation of reagent solubility in common organic solvents.
  • Assessing coupling yields and racemization levels in model reactions.
  • Comparison with previously reported coupling reagents.

Main Results:

  • The novel reagent exhibits enhanced solubility due to its carbocation moiety.
  • Superior coupling yields were achieved compared to previous reagents.
  • Significantly decreased racemization was observed.
  • The reagent's effectiveness allows for the use of only 1 equivalent of base.

Conclusions:

  • The novel proton acceptor coupling reagent offers significant advantages.
  • Its unique structure enhances solubility, coupling efficiency, and stereochemical control.
  • This reagent represents a valuable advancement in synthetic organic chemistry.