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Related Concept Videos

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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Elimination Reactions02:25

Elimination Reactions

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A nucleophile can react with an alkyl halide to give the substitution product by displacing the halogen. Or it can function as a base to give the elimination product by deprotonation of the neighboring carbon to form an alkene. In an elimination reaction, the substrate loses two groups from adjacent carbons forming at least one π bond. The carbon attached to the halogen is called the α carbon, while the adjacent carbon is called the β carbon; hence, these reactions are called...
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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...
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.2K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
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Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

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Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
2.0K
Amines to Alkenes: Hofmann Elimination01:16

Amines to Alkenes: Hofmann Elimination

2.4K
Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous...
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Updated: Jun 3, 2025

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Solvent-Dependent C(sp3)-CF3 Reductive Elimination from Neutral Four-Coordinate Cu(III) Complexes.

Yuecheng Weng1, Deng Pan1, Jian Wu1

  • 1Key Laboratory of Fluorine and Nitrogen Chemistry and Advanced Materials, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 9, 2025
PubMed
Summary

Copper(III) complexes undergo solvent-dependent C(sp3)-CF3 bond formation. Less polar solvents facilitate concerted reactions, while polar solvents involve ligand dissociation before bond formation, impacting copper-mediated trifluoromethylation mechanisms.

Keywords:
Cu(III)concerteddissociationmechanismreductive elimination

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Chemistry
  • Reaction Mechanisms

Background:

  • Copper(III) complexes are increasingly recognized for their catalytic potential.
  • Trifluoromethylation reactions are crucial for synthesizing pharmaceuticals and agrochemicals.
  • Understanding reaction mechanisms is key to optimizing synthetic routes.

Purpose of the Study:

  • To investigate the solvent-dependent mechanism of C(sp3)-CF3 bond formation from Cu(III) complexes.
  • To elucidate the role of solvent polarity in copper-mediated trifluoromethylation.
  • To provide insights into the reductive elimination pathways from neutral four-coordinate Cu(III) intermediates.

Main Methods:

  • Synthesis and characterization of neutral four-coordinate Cu(III) complexes.
  • Kinetic studies involving varying solvent polarity, ligand effects, and temperature.
  • Density Functional Theory (DFT) calculations to model reaction pathways.

Main Results:

  • Solvent polarity dictates the reaction mechanism: concerted elimination in less polar solvents (e.g., ClCH2CH2Cl) versus ligand dissociation followed by elimination in polar solvents (e.g., DMF).
  • Kinetic data and DFT calculations support distinct mechanistic pathways based on solvent choice.
  • The study identifies a rate-limiting ligand dissociation step in polar solvents.

Conclusions:

  • The mechanism of C(sp3)-CF3 bond formation from Cu(III) complexes is highly sensitive to solvent polarity.
  • This solvent-dependent reactivity offers opportunities for controlling copper-mediated trifluoromethylation outcomes.
  • The findings advance the understanding of organocopper chemistry and reductive elimination processes.