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Related Concept Videos

Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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β-Dicarbonyl Compounds via Crossed Claisen Condensations01:18

β-Dicarbonyl Compounds via Crossed Claisen Condensations

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Crossed Claisen condensations are base-promoted reactions between two different ester molecules producing β-dicarbonyl compounds. The reaction involving esters, with both containing α hydrogen, results in a mixture of four different products that are difficult to isolate. This reduces the synthetic utility of the reaction.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
Similar to cross-metathesis, ADMET also involves the formation of metallacyclobutane intermediate by [2+2] cycloaddition of one of the double bonds of a terminal diene with...
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.8K
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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Related Experiment Video

Updated: Apr 19, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
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Functionalized olefin cross-coupling to construct carbon-carbon bonds.

Julian C Lo1, Jinghan Gui1, Yuki Yabe1

  • 1Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, California 92037, USA.

Nature
|December 19, 2014
PubMed
Summary

This study introduces a new iron-catalyzed method for creating carbon-carbon bonds, essential in many chemicals. The reaction efficiently joins complex molecules under mild conditions, offering a practical approach for organic synthesis.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Carbon-carbon (C-C) bonds are fundamental to numerous vital molecules like polymers, dyes, and pharmaceuticals.
  • Developing efficient and practical methods for C-C bond formation is a key challenge in organic chemistry.
  • Existing methods often struggle with sensitive functional groups and sterically hindered environments.

Purpose of the Study:

  • To report a novel chemical transformation for the facile construction of highly substituted and uniquely functionalized C-C bonds.
  • To demonstrate a versatile method applicable to a wide range of substrates.
  • To provide a practical and chemoselective route to complex molecular architectures.

Main Methods:

  • Utilized a simple iron catalyst.
  • Employed an inexpensive silane as a reagent.
  • Conducted the reaction in a benign solvent under ambient atmosphere.
  • Reacted heteroatom-substituted olefins with electron-deficient olefins.

Main Results:

  • Successfully achieved the facile construction of C-C bonds.
  • Demonstrated the formation of highly substituted and uniquely functionalized molecular architectures.
  • Presented over 60 examples showcasing broad substrate scope.
  • Highlighted the reaction's chemoselectivity and mild reaction conditions.

Conclusions:

  • The reported iron-catalyzed reaction offers a facile and practical method for C-C bond formation.
  • This transformation enables access to previously difficult or impossible molecular architectures.
  • The method's mildness, chemoselectivity, and use of simple reagents make it highly valuable for organic synthesis.