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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Ziegler–Natta polymerization is another form of addition or chain‐growth polymerization used for synthesizing linear polymers over branched polymers. The catalyst used for polymerization is the Ziegler–Natta catalyst, named after Karl Ziegler and Giulio Natta, who developed it in 1953. This catalyst is an organometallic complex of titanium tetrachloride and triethyl aluminum, with the active form of the catalyst being an alkyl titanium compound. Using the Ziegler–Natta...
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Radical Chain-Growth Polymerization: Mechanism01:09

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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this...
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Introduction to Mechanisms of Enzyme Catalysis01:13

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For many years, scientists thought that enzyme-substrate binding took place in a simple "lock-and-key" fashion. This model stated that the enzyme and substrate fit together perfectly in one instantaneous step. However, current research supports a more refined view scientists call induced fit. The induced-fit model expands upon the lock-and-key model by describing a more dynamic interaction between enzyme and substrate. As the enzyme and substrate come together, their interaction causes...
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Radical Chain-Growth Polymerization: Overview01:10

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Chain-growth or addition polymerization is successive addition reactions of monomers with a polymer chain. In radical chain-growth polymerization, the reaction proceeds via a free-radical intermediate. The free radical is formed from radical initiators, which spontaneously generate free radicals by homolytic fission. Organic peroxides (such as dibenzoyl peroxide, as shown in Figure 1) or azo compounds are popular radical initiators. A low concentration ratio of radical initiator to monomer is...
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Millifluidics for Chemical Synthesis and Time-resolved Mechanistic Studies
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Unlocking the Chain-Walking Process in Gold Catalysis.

Vivek W Bhoyare1, Akash G Tathe1, Vincent Gandon2

  • 1Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, 462 066, Bhopal, India.

Angewandte Chemie (International Ed. in English)
|October 2, 2023
PubMed
Summary

Gold catalysts enable novel chain-walking reactions via Au(I)/Au(III) redox cycling. This breakthrough facilitates the annulation of alkenes and iodoarenes, expanding synthetic possibilities.

Keywords:
AnnulationChain-WalkingGold CatalysisMigratory Insertionβ-Hydride Elimination

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Area of Science:

  • Organometallic Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Gold catalysis has emerged as a powerful tool in organic synthesis.
  • Ligand-enabled redox catalysis, particularly involving Au(I)/Au(III) cycles, offers unique reactivity pathways.
  • Chain-walking reactions allow for the migration of functional groups along carbon chains, enabling complex molecular architectures.

Purpose of the Study:

  • To report the first successful gold-catalyzed chain-walking reactions.
  • To develop a novel gold-catalyzed annulation reaction between alkenes and iodoarenes.
  • To elucidate the mechanism of this new reactivity through experimental and computational investigations.

Main Methods:

  • Utilizing ligand-enabled Au(I)/Au(III) redox catalysis.
  • Employing a combination of alkenes and iodoarenes as substrates.
  • Conducting comprehensive experimental studies, including mechanistic probes.
  • Performing computational studies (e.g., DFT calculations) to understand reaction pathways.

Main Results:

  • Demonstrated the first instance of gold-catalyzed chain-walking reactions.
  • Developed a novel annulation reaction of alkenes with iodoarenes.
  • Showcased the interplay between chain-walking and π-activation reactivity modes.
  • Elucidated the reaction mechanism, providing insights into the catalytic cycle.

Conclusions:

  • The development of gold-catalyzed chain-walking reactions represents a significant advancement in synthetic methodology.
  • The newly developed annulation reaction offers a versatile route to complex molecules.
  • The mechanistic understanding provides a foundation for further catalyst design and reaction optimization.