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Related Concept Videos

Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.5K
The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
2.5K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
2.9K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.2K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.2K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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.
3.3K
Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

6.1K
Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
6.1K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.6K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.6K

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Electroreductive C(sp3)-C(sp3) Cross-Coupling Reactions.

Min Liu1, Wentao Zhang1, Pengfei Li1

  • 1State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

The Journal of Organic Chemistry
|November 11, 2025
PubMed
Summary
This summary is machine-generated.

Electrochemical reductive methods offer a green and selective approach for creating challenging C(sp³)-C(sp³) bonds in synthetic chemistry. This perspective highlights recent progress and future potential in this evolving field.

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Area of Science:

  • Synthetic organic chemistry
  • Electrochemistry
  • Green chemistry

Background:

  • Forming C(sp³)-C(sp³) bonds is a significant challenge in organic synthesis.
  • Conventional methods often require harsh reagents and conditions.
  • Electrochemistry presents a sustainable alternative using electricity as a clean redox agent.

Purpose of the Study:

  • To review recent advancements in electrochemical reductive C(sp³)-C(sp³) bond formation.
  • To provide insights into future research directions in this area.
  • To emphasize the benefits of electrochemistry in synthetic chemistry.

Main Methods:

  • Focuses on electrochemical reductive strategies.
  • Summarizes key literature in the field.
  • Discusses reaction mechanisms and selectivity.

Main Results:

  • Demonstrates the growing success of electrochemical methods for C(sp³)-C(sp³) coupling.
  • Highlights precise control over reaction selectivity.
  • Showcases environmental benefits and renewable energy integration.

Conclusions:

  • Electrochemical reductive approaches are a powerful tool for C(sp³)-C(sp³) bond construction.
  • The field shows significant promise for sustainable and efficient synthesis.
  • Further exploration of electrochemical methods is encouraged for synthetic chemists.