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Related Concept Videos

Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

As depicted in the figure below, the unsymmetrical ketones can form two possible enolates: less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are more stable. But the energy required to form kinetic enolates is less.
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
Acid-Catalyzed Dehydration of Alcohols to Alkenes02:35

Acid-Catalyzed Dehydration of Alcohols to Alkenes

In a dehydration reaction, a hydroxyl group in an alcohol is eliminated along with the hydrogen from an adjacent carbon. Here, the products are an alkene and a molecule of water. Dehydration of alcohols is generally achieved by heating in the presence of an acid catalyst. While the dehydration of primary alcohols requires high temperatures and acid concentrations, secondary and tertiary alcohols can lose a water molecule under relatively mild conditions.

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Updated: Jun 18, 2026

Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Regioselective iron-catalyzed decarboxylative allylic etherification.

Rushi Trivedi1, Jon A Tunge

  • 1Department of Chemistry, The University of Kansas, Lawrence, Kansas 66045, USA.

Organic Letters
|November 20, 2009
PubMed
Summary

An anionic iron complex efficiently catalyzes the decarboxylative allylation of phenols, producing allylic ethers. This iron-catalyzed reaction offers a cost-effective alternative to palladium catalysts for organic synthesis.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Decarboxylative allylation is a key transformation in organic synthesis.
  • Palladium catalysts are commonly used but are expensive.
  • Developing cost-effective alternatives is crucial for sustainable chemistry.

Purpose of the Study:

  • To develop an efficient iron-based catalyst for the decarboxylative allylation of phenols.
  • To investigate the catalytic mechanism and regioselectivity of the reaction.
  • To explore iron catalysts as a sustainable alternative to palladium.

Main Methods:

  • Synthesis of an anionic iron complex.
  • Catalytic decarboxylative allylation of various phenols.
  • Analysis of reaction products to determine yield and regioselectivity.
  • Mechanistic studies to probe the reaction pathway.

Main Results:

  • The anionic iron complex effectively catalyzed the decarboxylative allylation of phenols.
  • High yields of allylic ethers were obtained.
  • The reaction exhibited regioselectivity, suggesting a pi-allyl iron intermediate pathway.
  • Iron catalysts demonstrated potential to replace expensive palladium catalysts.

Conclusions:

  • Anionic iron complexes are effective catalysts for decarboxylative allylation of phenols.
  • The reaction mechanism likely involves pi-allyl iron intermediates.
  • Iron catalysis presents a promising, cost-effective alternative to palladium in decarboxylative couplings.