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Related Concept Videos

Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.2K
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

1.9K
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
1.9K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

2.8K
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.
2.8K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

4.0K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
4.0K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.7K
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.
3.7K
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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

2.2K
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.
2.2K

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Related Experiment Video

Updated: Sep 9, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Photo-Mediated Silacyclization by Wavelength-Dependent Selective C─F or C─H Functionalization.

Gan Wang1, Ye Yuan1, Chu Wang1

  • 1Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, 117543, Singapore.

Angewandte Chemie (International Ed. in English)
|September 1, 2025
PubMed
Summary

Researchers developed a new photo-mediated silacyclization method using specific LED wavelengths to create valuable benzosilacycles. This approach enables selective C-F and C-H functionalization for diverse applications.

Keywords:
CyclizationHeterocyclesHydrogen evolutionPhotocatalysisSilicon

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Area of Science:

  • Organosilicon Chemistry
  • Photocatalysis
  • Synthetic Organic Chemistry

Background:

  • Silacycles are crucial in medicinal chemistry and materials science.
  • Defluorosilylation of aryl fluorides and selective arene silylation are synthetically challenging.
  • Existing methods often require external oxidants or struggle with selectivity.

Purpose of the Study:

  • To develop a novel photo-mediated cascade silacyclization for constructing six-membered benzosilacycles.
  • To achieve selective C-F and C-H functionalization of allylbenzene derivatives using wavelength control.
  • To explore a sustainable and versatile synthesis of silacycle compounds.

Main Methods:

  • Utilized a synergistic system of an organophotocatalyst and a thiol-based hydrogen atom transfer (HAT) catalyst.
  • Employed specific light-emitting diode (LED) wavelengths (456 and 335 nm) to mediate the cascade reaction.
  • Investigated mechanistic pathways including HAT-facilitated hydrosilylation and wavelength-dependent intramolecular silacyclization.

Main Results:

  • Successfully achieved wavelength-dependent photo-mediated cascade silacyclization of allylbenzene derivatives with dihydrosilanes.
  • Demonstrated the first defluorosilacyclization of ortho-fluoroallylbenzenes and acceptorless dehydrosilacyclization.
  • Uncovered a light-assisted hydrogen evolution process during cascade C-H silacyclization.

Conclusions:

  • The developed photo-mediated strategy offers precise wavelength-dependent chemoselectivity for silacycle synthesis.
  • The method exhibits broad functional group tolerance and provides a sustainable route to valuable silacycle compounds.
  • This work advances the synthetic utility of silacycles through innovative photocatalytic approaches.