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Related Concept Videos

Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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Voltage Doubler Circuit01:23

Voltage Doubler Circuit

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A voltage doubler circuit integrates two main components: a clamping section and a rectifier section. The clamping section consists of a capacitor (C1) and a diode (D1), whereas the rectifier section is equipped with another diode (D2) and capacitor (C2). This circuit produces an output voltage with twice the amplitude of the sinusoidal input voltage.
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Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
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Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
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Generator Voltage Control01:21

Generator Voltage Control

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Generator voltage control is crucial for maintaining the stable operation of synchronous generators and wind turbines. In older models, a DC generator driven by the rotor delivers DC power to the rotor's field winding, and the power is transferred through slip rings and brushes. In the latest models, static or brushless exciters are used. Static exciters rectify AC power from the generator terminals and then transfer the DC power directly to the rotor. Brushless exciters, on the other hand,...
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

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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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A Voltage-Controlled Strategy for Modular Shono-Type Amination.

Siyuan Su1, Yahui Guo1, Bryan Parnitzke1

  • 1Department of Chemistry, Boston University, Boston, Massachusetts 02215, United States.

Journal of the American Chemical Society
|October 14, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces a voltage-controlled electrooxidation method for creating functionalized heterocycles. This approach overcomes limitations of previous methods, enabling broader scope C-N bond formation using diverse amine nucleophiles.

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Area of Science:

  • Organic Chemistry
  • Electrochemistry
  • Medicinal Chemistry

Background:

  • Shono-type oxidation is key for late-stage pharmacophore diversification.
  • Existing methods are limited by potential drift in constant current electrolysis, restricting nucleophile scope.
  • Development beyond oxygen nucleophiles is needed for broader synthetic applications.

Purpose of the Study:

  • To develop a voltage-controlled electrooxidation strategy for C-N bond formation.
  • To enable selective oxidation of a broad range of amine nucleophiles for heterocyclic synthesis.
  • To overcome limitations associated with constant current electrolysis in Shono-type reactions.

Main Methods:

  • Electroanalytical techniques including cyclic voltammetry (CV) and differential pulse voltammetry (DPV) were used to determine substrate oxidation potentials.
  • Controlled potential electrolysis (CPE) was implemented to selectively oxidize protected amine nucleophiles.
  • A systematic comparison between CPE and constant current electrolysis (CCE) was performed.

Main Results:

  • A voltage-controlled strategy enabled modular C-N bond formation with carbamate-, sulfonamide-, and benzamide-derived nucleophiles.
  • CPE provided moderate to good yields of α-functionalized C-N products, demonstrating improved selectivity over CCE.
  • The method successfully functionalized sulfonamide drugs and enabled sequential C-N and C-O functionalization.

Conclusions:

  • Voltage-controlled electrolysis is crucial for selective and high-yielding Shono-type oxidations.
  • This method significantly expands the scope of nucleophiles applicable in electrooxidative C-N bond formation.
  • The developed strategy offers a powerful tool for late-stage diversification of heterocyclic compounds, including drug molecules.