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Related Concept Videos

Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

4.0K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
4.0K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

4.6K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

3.7K
The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
3.7K
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

6.4K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
6.4K
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

10.1K
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.
10.1K
Halogenation of Alkenes02:46

Halogenation of Alkenes

18.3K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
18.3K

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Organophotoredox-Catalyzed Alkene Functionalization Reactions Using α-Bromocarbonyl Compounds.

Yasunori Toda1, Koyo Ono1, Ryunosuke Fujimaki1

  • 1Department of Materials Chemistry, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan.

Organic Letters
|December 3, 2025
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Summary
This summary is machine-generated.

Visible-light organophotoredox catalysis enables carbolactonization of alkenoic acids with α-bromocarbonyl compounds. This method generates carbon radicals for C-H functionalization, offering a novel synthetic pathway.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Photochemistry

Background:

  • Carbolactonization is a crucial reaction in organic synthesis.
  • Developing efficient catalytic methods for carbolactonization is an ongoing challenge.
  • Visible-light organophotoredox catalysis offers a sustainable approach to chemical transformations.

Purpose of the Study:

  • To report the first visible-light organophotoredox-catalyzed carbolactonization of alkenoic acids with α-bromocarbonyl compounds.
  • To explore the application of this protocol in C-H functionalization reactions.
  • To elucidate the reaction mechanism.

Main Methods:

  • Visible-light irradiation
  • Organophotoredox catalysis using a phosphonium ylide photocatalyst
  • Reaction with alkenoic acids and α-bromocarbonyl compounds
  • C-H functionalization of 1,1-diphenylethylene and 3-methylindole
  • Radical and fluorescence quenching experiments

Main Results:

  • Successful carbolactonization of alkenoic acids with α-bromocarbonyl compounds under visible-light.
  • Generation of carbon-centered radicals from α-bromocarbonyl compounds.
  • Application of the protocol to C-H functionalization of challenging substrates.
  • Support for the proposed catalytic cycle through mechanistic studies.

Conclusions:

  • A novel and efficient visible-light organophotoredox-catalyzed carbolactonization reaction has been developed.
  • The methodology provides a new route for synthesizing valuable organic compounds.
  • The study offers insights into the mechanism of photoredox-catalyzed radical reactions.