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Related Concept Videos

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

2.4K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
2.4K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.4K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
2.4K
Properties of Organometallic Compounds01:23

Properties of Organometallic Compounds

2.2K
Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.
2.2K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.3K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
5.3K
Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

3.4K
Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.
Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs,...
3.4K
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

4.5K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the...
4.5K

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Related Experiment Video

Updated: Apr 17, 2026

Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

Published on: March 20, 2017

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Alkali metal mediated C-C bond coupling reaction.

Hiroto Tachikawa1

  • 1Division of Materials Chemistry, Graduate School of Engineering, Hokkaido University, Kita-ku, Sapporo 060-8628, Japan.

The Journal of Chemical Physics
|February 16, 2015
PubMed
Summary

Investigating electron and hole capture in lithium-benzene complexes reveals a new carbon-carbon bond forms upon electron capture. This finding offers insights into metal-catalyzed reactions crucial for organic chemistry and pharmaceuticals.

Area of Science:

  • Computational chemistry
  • Physical chemistry
  • Materials science

Background:

  • Metal-catalyzed carbon-carbon bond formation is vital in organic synthesis and pharmaceutical development.
  • Understanding reaction dynamics at the molecular level is key to optimizing chemical processes.

Purpose of the Study:

  • To investigate the electron and hole capture dynamics of the lithium-benzene sandwich complex, Li(Bz)2.
  • To elucidate the mechanism of carbon-carbon bond formation in this system.

Main Methods:

  • Direct ab-initio molecular dynamics simulations were employed.
  • The study focused on analyzing structural changes and vibrational enhancements upon electron and hole capture.

Main Results:

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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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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

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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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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene

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

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Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
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  • Electron capture by Li(Bz)2 induced significant structural changes, including rapid fluctuations and the formation of a new C-C single bond between benzene rings.
  • Hole capture primarily enhanced intermolecular vibrations between the benzene rings without C-C bond formation.

    • Conclusions:

    • The theoretical results highlight a distinct mechanism for C-C bond formation driven by electron capture in Li(Bz)2.
    • This study provides fundamental insights into the electronic and structural dynamics governing C-C bond formation in organometallic complexes.