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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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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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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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Cycloaddition Reactions: Overview01:16

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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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Atomically Dispersed Palladium Promoted Suzuki-Miyaura Cross Coupling.

Junhao Huang1, Marcus Klahn1, Stephan Bartling1

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Chemsuschem
|September 10, 2025
PubMed
Summary

This study introduces a palladium catalyst on polymeric carbon nitride (Pd/PCN) for efficient Suzuki-Miyaura cross-coupling reactions at room temperature. Isolated palladium species on Pd/PCN show higher activity than nanoparticles, with performance influenced by reaction atmosphere.

Keywords:
Suzuki couplingattenuated total reflection‐Fourier transform infrared spectroscopyheterogeneous Pd catalystspolymeric carbon nitride

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Catalysis

Background:

  • The Suzuki-Miyaura cross-coupling reaction is a cornerstone of modern organic synthesis for forming carbon-carbon bonds.
  • Developing efficient, stable, and recyclable catalysts is crucial for sustainable chemical synthesis.
  • Palladium catalysts are widely used but can be expensive and prone to aggregation.

Purpose of the Study:

  • To report a novel isolated palladium catalyst supported on polymeric carbon nitride (Pd/PCN).
  • To investigate the efficiency of the Pd/PCN catalyst in Suzuki-Miyaura cross-coupling reactions at room temperature.
  • To explore the effect of palladium species size and reaction atmosphere on catalytic performance.

Main Methods:

  • Synthesis of palladium catalyst supported on polymeric carbon nitride (Pd/PCN).
  • Suzuki-Miyaura cross-coupling reaction of bromobenzene and phenylboronic acid.
  • Characterization of catalyst activity, including mole-specific activity and effect of Pd size (isolated species vs. nanoparticles).
  • Continuous flow tests to evaluate catalyst stability and performance under different atmospheres (O2 vs. Ar).
  • In-situ infrared spectroscopy for mechanistic investigations.

Main Results:

  • The Pd/PCN catalyst demonstrated efficient Suzuki-Miyaura cross-coupling of bromobenzene and phenylboronic acid at room temperature.
  • A 2 wt% Pd loading on the Pd/PCN catalyst achieved the highest mole-specific activity.
  • Isolated palladium species exhibited higher catalytic activity compared to palladium nanoparticles.
  • Catalyst performance was sensitive to the reaction atmosphere, with increased side reactions (self-coupling) under O2 flow.
  • Mechanistic studies revealed the role of K2CO3 in activating phenylboronic acid.

Conclusions:

  • Isolated palladium species supported on polymeric carbon nitride represent a highly active catalyst for Suzuki-Miyaura cross-coupling.
  • The catalyst offers an efficient route for carbon-carbon bond formation under mild, room-temperature conditions.
  • Understanding the influence of reaction atmosphere and catalyst morphology is key to optimizing cross-coupling reactions.