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Related Concept Videos

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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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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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

2.1K
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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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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Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.1K
Radical Formation: Overview01:03

Radical Formation: Overview

2.6K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Carbon-Heteroatom Bond Formation via Photoinduced Decarboxylative Radical Coupling Reactions.

Danilo F C de Benedicto1, Giovanna S Tâmega1, Mateus O Costa1

  • 1Laboratory of Synthesis, Catalysis, and Modeling (SintCatMol), Chemistry Department, Federal University of São Carlos (UFSCar), Rodovia Washington Luís, km 235 - SP - 310, São Carlos, São Paulo 13565-905, Brazil.

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This review explores photoinduced decarboxylative coupling using free carboxylic acids to form C-heteroatom bonds. It highlights sustainable methods for radical generation, advancing organic synthesis.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Sustainable Synthesis

Background:

  • Carboxylic acids are vital feedstock chemicals in organic synthesis.
  • Decarboxylation is a key strategy for forming C-C and C-heteroatom bonds.
  • Current methods often require carboxylic acid activation, limiting cost-effectiveness and sustainability.

Purpose of the Study:

  • To provide a comprehensive overview of photoinduced decarboxylative coupling reactions.
  • To focus on reactions utilizing free carboxylic acids as radical precursors.
  • To critically assess mechanistic insights, advantages, limitations, and future potential.

Main Methods:

  • Review of literature on photoinduced decarboxylative coupling reactions.
  • Analysis of mechanistic pathways for C-heteroatom bond formation.
  • Evaluation of reaction efficiency, scope, and sustainability.

Main Results:

  • Photoinduced decarboxylation of free carboxylic acids offers a sustainable route to C-heteroatom bonds.
  • Mechanistic understanding is crucial for optimizing these reactions.
  • Various strategies exist, each with specific benefits and drawbacks.

Conclusions:

  • Photoinduced decarboxylative coupling with free carboxylic acids is a promising area for sustainable organic synthesis.
  • Further research can enhance efficiency, broaden applicability, and improve cost-effectiveness.
  • This approach offers significant potential for greener chemical transformations.