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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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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 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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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.
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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...
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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Intermolecular Electrophilic Germylation Using GeCl4 and Al2Cl6.

Justyna Łosiewicz1, Milan Kumar Bisai1, Zachary A Bub1

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, UK.

Angewandte Chemie (International Ed. in English)
|April 13, 2026
PubMed
Summary
This summary is machine-generated.

Researchers developed the first effective intermolecular Germa-Friedel-Crafts reaction. This new method uses germanium tetrachloride and a pyridine base for efficient C-H germylation of arenes, enabling selective synthesis of aryl germanes.

Keywords:
C–H germylationLewis acidsaluminum trichlorideelectrophilic substitutiongermanium

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Area of Science:

  • Organometallic Chemistry
  • Organic Synthesis
  • Main Group Chemistry

Background:

  • Electrophilic aromatic substitution is well-established for lighter Group 14 elements.
  • Electrophilic germylation remains significantly underdeveloped compared to acylation, alkylation, and silylation.

Purpose of the Study:

  • To report the first effective intermolecular Germa-Friedel-Crafts reaction.
  • To develop a method for electrophilic C-H germylation of arenes.

Main Methods:

  • Utilized germanium tetrachloride (GeCl4) as the key industrial precursor.
  • Employed aluminum chloride (Al2Cl6) as a halophilic activator.
  • Incorporated an inexpensive hindered pyridine base to facilitate the reaction.

Main Results:

  • Achieved the first effective intermolecular Germa-Friedel-Crafts reaction.
  • Enabled selective synthesis of mono-aryl germanes (ArGeCl3) and di-aryl germanes (Ar2GeCl2).
  • Demonstrated in situ transformation of ArGeCl3 into synthetically useful ArGe(alkyl)3 derivatives.

Conclusions:

  • The developed process allows for high-yielding electrophilic C-H germylation of arenes.
  • The reaction proceeds via an SEAr-type mechanism, facilitated by Al2Cl6 activation and a Brønsted base.
  • This work establishes a viable route for intermolecular germylation, overcoming previous limitations.