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Related Concept Videos

Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.1K
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...
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Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene01:14

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

2.5K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.5K
Halogenation of Alkenes02:46

Halogenation of Alkenes

15.6K
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.
15.6K
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

8.1K
Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
8.1K
Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

4.8K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
4.8K
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

5.6K
The electrophilic addition of hydrogen halides such as HBr to alkenes and nonconjugated dienes gives a single product as per Markovnikov’s rule.
5.6K

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Related Experiment Video

Updated: Jun 28, 2025

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Silver Surface-Assisted Dehydrobrominative Cross-Coupling between Identical Aryl Bromides.

Zhen-Yu Yi1,2, Zi-Cong Wang1,2, Ruo-Ning Li1,2

  • 1CAS Key Laboratory of Molecular Nanostructure and Nanotechnology, CAS Research/Education Center for Excellence in Molecular Sciences, Beijing National Laboratory for Molecular Sciences (BNLMS), Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

Journal of the American Chemical Society
|April 10, 2024
PubMed
Summary
This summary is machine-generated.

Researchers achieved selective dehydrobrominative cross-coupling of identical molecules on silver surfaces. This unexpected reaction provides new synthetic tools and mechanistic insights into surface-catalyzed coupling reactions.

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

  • Surface Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Cross-coupling reactions are vital in chemical synthesis.
  • Achieving selectivity with similar or identical precursors remains a challenge.

Purpose of the Study:

  • To report an unexpected dehydrobrominative cross-coupling reaction between identical molecules.
  • To investigate the selectivity and mechanism of this reaction on silver surfaces.

Main Methods:

  • Scanning tunneling microscopy (STM) for single-molecule analysis.
  • Quantification of reaction selectivity.
  • Theoretical calculations for mechanistic insights.

Main Results:

  • Demonstrated selective dehydrobrominative cross-coupling of 1,3,5-tris(2-bromophenyl)benzene (TBPB) on silver.
  • Identified substrate lattice activity and molecular assembly as selectivity modulators.
  • Revealed a mechanism involving regioselective C-H activation and radical C-C coupling.

Conclusions:

  • The study expands synthetic methodologies for selective coupling reactions.
  • Provides crucial mechanistic understanding of surface-catalyzed reactions and selectivity.
  • Highlights the role of reaction kinetics in achieving selectivity.