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Related Concept Videos

Halogenation of Alkenes02:46

Halogenation of Alkenes

16.9K
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.
16.9K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

10.5K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
10.5K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

3.7K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.7K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

9.0K
Introduction
Halogenation is another class of electrophilic addition reactions where a halogen molecule gets added across a π bond. In alkynes, the presence of two π bonds allows for the addition of two equivalents of halogens (bromine or chlorine). The addition of the first halogen molecule forms a trans-dihaloalkene as the major product and the cis isomer as the minor product. Subsequent addition of the second equivalent yields the tetrahalide.
9.0K
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.7K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.7K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.0K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
2.0K

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Copper-catalyzed radical ring-opening halogenation with HX.

Shuai Liu1, Ming Bai, Peng-Fei Xu

  • 1Department of Chemistry, School of Chemistry, Xi'an Key Laboratory of Sustainable Energy Material Chemistry and MOE Key Laboratory for Nonequilibrium Synthesis and Modulation of Condensed Matter, Xi'an Jiaotong University, Xi'an 710049, China. guoln81@xjtu.edu.cn.

Chemical Communications (Cambridge, England)
|August 10, 2021
PubMed
Summary

A new copper-catalyzed method enables radical ring-opening halogenation of alkyl ketones and nitriles using aqueous hydrohalic acids. This green chemistry approach provides efficient access to valuable halogenated organic compounds.

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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Radical reactions are crucial in organic synthesis.
  • Halogenated compounds are important building blocks.
  • Efficient and sustainable synthetic methods are needed.

Purpose of the Study:

  • To develop a novel copper-catalyzed radical ring-opening halogenation protocol.
  • To utilize green halogen sources and redox-neutral conditions.
  • To provide practical access to distally halogenated alkyl ketones and nitriles.

Main Methods:

  • Copper-catalyzed radical reaction.
  • Ring-opening of cyclic precursors.
  • Halogenation using aqueous hydrohalic acids (HX).

Main Results:

  • Successful synthesis of chlorinated, brominated, and iodinated alkyl ketones and nitriles.
  • Broad substrate scope demonstrated.
  • Moderate to good yields achieved under redox-neutral conditions.

Conclusions:

  • The described protocol offers an efficient and green method for synthesizing distally halogenated compounds.
  • This approach expands the utility of copper catalysis in radical reactions.
  • The method provides a practical route to valuable halogenated intermediates.