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Conjugate Addition of Enolates: Michael Addition01:08

Conjugate Addition of Enolates: Michael Addition

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The attack of a nucleophile at the β carbon of an α,β-unsaturated carbonyl compound is called conjugate addition. Conjugate addition reactions of active methylene compounds, such as β-diketones, β-keto esters, β-keto nitriles, and α-nitro ketones, are called Michael addition reactions.
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Introduction to Electrophilic Addition Reactions of Alkenes02:24

Introduction to Electrophilic Addition Reactions of Alkenes

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The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...
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Halogenation of Alkenes02:46

Halogenation of Alkenes

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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.
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Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

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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.
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Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

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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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Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene01:17

Electrophilic 1,2- and 1,4-Addition of HX to 1,3-Butadiene

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The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
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Updated: Feb 20, 2026

Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides
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Efficient Synthesis of All-Carbon Quaternary Centers via the Conjugate Addition of Functionalized Monoorganozinc Bromides

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A halogen-bonding-catalyzed Michael addition reaction.

Jan-Philipp Gliese1, Stefan H Jungbauer, Stefan M Huber

  • 1Department of Chemistry and Biochemistry, Ruhr-Universität Bochum, Universitätsstraße 150, 44801 Bochum, Germany. stefan.m.huber@rub.de.

Chemical Communications (Cambridge, England)
|October 25, 2017
PubMed
Summary

Researchers explored halogen bonding in catalysis using (benz)imidazolium compounds for Michael addition reactions. A novel atropisomeric catalyst significantly accelerated the reaction by approximately 50 times.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Supramolecular Chemistry

Background:

  • Halogen bonding is an underutilized non-covalent interaction in catalysis.
  • Development of efficient halogen bond donors is crucial for expanding catalytic applications.

Purpose of the Study:

  • To investigate the efficacy of (benz)imidazolium-based compounds as halogen bond donors in catalysis.
  • To design and synthesize novel halogen bond donors for enhanced catalytic activity.

Main Methods:

  • Synthesis of (benz)imidazolium-based halogen bond donors.
  • Application of these donors as catalysts in the Michael addition reaction.
  • Evaluation of catalytic activity and rate acceleration.

Main Results:

  • Several (benz)imidazolium derivatives were successfully employed as halogen bond donors.
  • A rigid atropisomer featuring two iodobenzimidazolium moieties demonstrated potent catalytic activity.
  • This catalyst achieved a rate acceleration of approximately 50-fold compared to a reference.

Conclusions:

  • The study highlights the potential of (benz)imidazolium-based compounds as effective halogen bond donors in catalysis.
  • The developed atropisomeric catalyst represents a significant advancement in halogen bonding catalysis.
  • Further exploration of halogen bonding in organic synthesis is warranted.