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Lewis Acids and Bases02:16

Lewis Acids and Bases

13.9K
This lesson delves into Lewis acids and bases in the context of the octet rule for electron-deficient compounds. Here, the concept is discussed, emphasizing the group 13 elements like boron or aluminium. Since group 13 elements possess three valence electrons, they form trivalent compounds with a sextet of electrons and a vacant orbital for the central atom. Consequently, these electron-deficient compounds accept electrons from other species to complete their octet in a chemical reaction. They...
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Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

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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 carbon–oxygen...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

5.9K
Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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ortho–para-Directing Deactivators: Halogens01:24

ortho–para-Directing Deactivators: Halogens

5.5K
Halogens are ortho–para directors. They are more electronegative than carbon. Therefore, as ring substituents, they can withdraw electrons through the inductive effect and deactivate the aromatic ring towards electrophilic substitution. Halogens also have an electron-donating resonance effect on the ring, which influences the orientation of the incoming electrophile. If an electrophile attacks at the ortho or the para position, the halogen donates electrons and stabilizes the intermediate...
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Acid Halides to Alcohols: Grignard Reaction01:15

Acid Halides to Alcohols: Grignard Reaction

2.1K
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,...
2.1K
Acid Halides to Alcohols: LiAlH4 Reduction01:19

Acid Halides to Alcohols: LiAlH4 Reduction

2.7K
Acid halides are reduced to alcohols in the presence of a strong reducing agent like lithium aluminum hydride.
The mechanism proceeds in three steps. First, the nucleophilic hydride ion attacks the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs as a leaving group, generating an aldehyde. A second nucleophilic attack by the hydride yields an alkoxide ion, which, upon protonation, gives a primary alcohol as...
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Characterizing Lewis Pairs Using Titration Coupled with In Situ Infrared Spectroscopy
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Chlorodefluorination Induced by Gallium-Based Lewis Acids.

Katharina Tölke1, Beate Neumann1, Hans-Georg Stammler1

  • 1Universität Bielefeld, Fakultät für Chemie, Centrum für Molekulare Materialien, Universitätsstraße 25, 33615, Bielefeld, Germany.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|September 19, 2024
PubMed
Summary

Researchers synthesized a new gallium compound, [Ga(CCl2CF3)3(FSiMe3)], by selectively replacing fluorine atoms with chlorine. This compound shows potential as a catalyst for chlorodefluorination reactions.

Keywords:
ChlorodefluorinationC−F activationGalliumLewis super acidMain-group elements

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Area of Science:

  • Organometallic chemistry
  • Fluorine chemistry
  • Catalysis

Background:

  • Organogallium compounds are versatile reagents in synthetic chemistry.
  • Fluorinated organic compounds present unique synthetic challenges and opportunities.
  • Selective halogen exchange reactions are crucial for functional group transformations.

Purpose of the Study:

  • To synthesize and characterize a novel gallium-containing compound with fluorinated alkyl ligands.
  • To investigate the reactivity of this new compound, particularly its potential for halogen exchange.
  • To explore the catalytic applications of the synthesized compound in chlorodefluorination reactions.

Main Methods:

  • Reaction of [Ga(C2F5)3(FSiMe3)] with chlorotrimethylsilane.
  • Isolation and structural characterization of the resulting chlorogallate ion as a tetraphenylphosphonium salt.
  • Testing the catalytic activity in chlorodefluorination of various fluorinated substrates.

Main Results:

  • Selective substitution of alpha-fluorine atoms by chlorine atoms was achieved, forming [Ga(CCl2CF3)3(FSiMe3)].
  • The chlorogallate ion, [Ga(CCl2CF3)3Cl]-, was successfully isolated and structurally characterized.
  • [Ga(CCl2CF3)3(FSiMe3)] demonstrated catalytic activity in the chlorodefluorination of Me3SiCF3, 2,2-difluoropropane, and [PPh4][Ga(C2F5)4].

Conclusions:

  • A novel organogallium compound with selectively chlorinated fluorinated ligands was synthesized.
  • The structural characterization confirmed the successful halogen exchange.
  • The compound exhibits promising catalytic activity for chlorodefluorination, opening avenues for new synthetic methodologies.