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Related Concept Videos

Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

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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
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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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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.
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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

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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.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control01:23

Electrophilic Addition of HX to 1,3-Butadiene: Thermodynamic vs Kinetic Control

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The addition of a hydrogen halide to 1,3-butadiene gives a mixture of 1,2- and 1,4-adducts. Since more substituted alkenes are more stable, the 1,4-adduct is expected to be the major product. However, the product distribution is strongly influenced by temperature; low temperature favors the 1,2-adduct, whereas the 1,4-adduct is predominant at high temperature.
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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
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Controllable Remote C-H Bond Functionalization by Visible-Light Photocatalysis.

Xiao-Qiang Hu1, Jia-Rong Chen1, Wen-Jing Xiao1

  • 1CCNU-uOttawa Joint Research Center, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei, 430079, China.

Angewandte Chemie (International Ed. in English)
|January 21, 2017
PubMed
Summary

New strategies activate remote C(sp3)-H bonds using photoredox-catalyzed radical translocation. This enables controlled, site-selective functionalization of inert bonds, opening new reaction design avenues.

Keywords:
C−H functionalizationalkylationhydrogen atom transferphotoredox catalysisradicals

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Reaction Mechanisms

Background:

  • C(sp3)-H bonds are ubiquitous but challenging to functionalize selectively.
  • Existing methods often lack control over remote C(sp3)-H bond activation.
  • Photoredox catalysis offers a powerful platform for radical generation and transformations.

Purpose of the Study:

  • To develop novel strategies for the remote activation of C(sp3)-H bonds.
  • To enable site-selective functionalization of inert hydrocarbon frameworks.
  • To expand the toolkit for designing new chemical reactions.

Main Methods:

  • Utilizing photoredox-catalyzed (PC) radical translocation.
  • Employing O- and N-centered radicals as key intermediates.
  • Investigating hydrogen atom transfer (HAT) mechanisms.

Main Results:

  • Demonstrated successful activation of remote C(sp3)-H bonds.
  • Achieved controlled and site-selective functionalization.
  • Established new pathways for radical translocation in organic synthesis.

Conclusions:

  • Photoredox-catalyzed radical translocation provides an effective strategy for remote C(sp3)-H bond activation.
  • These methods offer significant potential for complex molecule synthesis and drug discovery.
  • The described approaches represent a significant advancement in synthetic methodology.