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Halogenation of Alkenes02:46

Halogenation of Alkenes

16.1K
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.
16.1K
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

2.6K
Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.
2.6K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.0K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.0K
Electrophilic Addition to Alkynes: Halogenation02:38

Electrophilic Addition to Alkynes: Halogenation

8.5K
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.
8.5K
Reactions at the Benzylic Position: Halogenation01:11

Reactions at the Benzylic Position: Halogenation

2.7K
Benzylic halogenation takes place under conditions that favor radical reactions such as heat, light, or a free radical initiator like peroxide.
2.7K
Radical Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.3K
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...
2.3K

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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Versatile halogenation via a CNHC^Csp3 palladacycle intermediate.

Qiaoqiao Teng1, Ziwei Liu1, Haobin Song1

  • 1Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology, School of Petrochemical Engineering, Changzhou University, Changzhou, 213164, China. tqq@cczu.edu.cn.

Dalton Transactions (Cambridge, England : 2003)
|February 13, 2023
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Summary

Researchers synthesized stable cyclopalladated complexes with a C-Pd bond using N-alkyl carbene ligands. These complexes show strong electron-donating properties and undergo versatile C-halogenation reactions.

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Palladium N-Heterocyclic Carbene Complexes: Synthesis from Benzimidazolium Salts and Catalytic Activity in Carbon-carbon Bond-forming Reactions
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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Cyclopalladated complexes are important in catalysis.
  • Carbene ligands play a crucial role in stabilizing metal complexes.
  • Electron-withdrawing substituents can influence ligand properties.

Purpose of the Study:

  • To synthesize novel stable cyclopalladated complexes.
  • To investigate the electronic properties of novel carbene ligands.
  • To explore the reactivity of these complexes in C-halogenation.

Main Methods:

  • Synthesis of cyclopalladated complexes via α-CH2 deprotonation and palladation.
  • Characterization of N-alkyl carbene ligands with electron-withdrawing substituents.
  • Experimental determination of electron-donating strengths.
  • Template-directed C-halogenation reactions with X2.

Main Results:

  • Stable cyclopalladated complexes featuring an (sp3)C-Pd bond were successfully synthesized.
  • The resulting CNHC^Csp3 chelators exhibited strong electron-donating strengths.
  • The palladacycle demonstrated versatile C-halogenation reactivity directed by the template.

Conclusions:

  • The study presents a novel route to stable cyclopalladated complexes.
  • The electron-donating ability of the new chelators was confirmed.
  • The developed methodology allows for versatile functionalization of the palladacycle.