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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Pericyclic Reactions: Introduction01:17

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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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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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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Limitations of Friedel–Crafts Reactions01:26

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Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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Palladium-Mediated C(sp

Shih-Yun Chen1, Rong Chang2, Zhong-Xin Lin1

  • 1Department of Applied Science, National Taitung University, Taitung, Taiwan 95092, R.O.C.

The Journal of Organic Chemistry
|June 5, 2023
PubMed
Summary

This study introduces a new palladium-catalyzed method for synthesizing substituted benzamides by activating C(sp3)-H bonds. This facile approach yields diverse N-(CH2-aryl/alkyl)-N-(pyridin-2-yl)benzamides with broad functional group compatibility.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Palladium-catalyzed reactions are crucial in modern organic synthesis.
  • C(sp3)-H bond activation offers an efficient route to functionalize aliphatic carbons.
  • Developing novel synthetic strategies for complex molecules remains a key challenge.

Purpose of the Study:

  • To develop a facile synthetic methodology for N-(CH2-aryl/alkyl)-substituted N-(pyridin-2-yl)benzamides.
  • To explore palladium-mediated C(sp3)-H bond activation for this transformation.
  • To demonstrate the utility of the synthesized compounds and propose a synthetic pathway to 2-aminopyridine derivatives.

Main Methods:

  • Palladium(II) acetate-mediated C(sp3)-H bond activation of N-methyl-N-(pyridin-2-yl)benzamide.
  • Formation and structural elucidation of dinuclear palladacycle intermediates using mass spectrometry, NMR spectroscopy, and X-ray crystallography.
  • Density functional theory calculations and kinetic isotope effect experiments to propose a reaction mechanism.

Main Results:

  • Successful synthesis of a range of N-(CH2-aryl/alkyl)-substituted N-(pyridin-2-yl)benzamides.
  • Demonstrated good functional group tolerance in the C(sp3)-H functionalization step.
  • Elucidation of key dinuclear palladacycle intermediates.
  • Proposed a plausible reaction mechanism supported by computational and experimental data.
  • Successfully converted N-(CH2-aryl)-N-(pyridin-2-yl)benzamides to N-(CH2-aryl)-2-aminopyridines via debenzoylation.

Conclusions:

  • A facile and efficient palladium-catalyzed method for C(sp3)-H activation and functionalization has been established.
  • The methodology allows for the synthesis of diverse N-(CH2-aryl/alkyl)-substituted N-(pyridin-2-yl)benzamides with broad substrate scope.
  • The developed route provides access to valuable 2-aminopyridine derivatives.