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Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

3.7K
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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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.5K
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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Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.9K
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...
4.9K
Amines to Alkenes: Cope Elimination01:14

Amines to Alkenes: Cope Elimination

2.3K
Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.
2.3K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

3.2K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
3.2K

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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C(sp3)-CF3 Reductive Elimination from a Five-Coordinate Neutral Copper(III) Complex.

Shuanshuan Liu1,2, He Liu2, Shihan Liu3

  • 1Shandong Provincial Key Laboratory of Fluorine Chemistry and Chemical Materials, School of Chemistry and Chemical Engineering, University of Jinan, Jinan 250022, China.

Journal of the American Chemical Society
|May 5, 2020
PubMed
Summary
This summary is machine-generated.

Researchers isolated a stable copper(III) complex that forms carbon-carbon bonds via reductive elimination. This fundamental catalytic process, previously unexplored for copper(III), offers new pathways for chemical synthesis.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Synthetic Chemistry

Background:

  • Reductive elimination from high-valent late-transition metals is crucial for C-C and C-heteroatom bond formation in catalysis.
  • While studied for Pt(IV), Pd(IV), Ni(III)/Ni(IV), and Au(III), reductive elimination from neutral Cu(III) complexes is largely unexplored.

Purpose of the Study:

  • To report the isolation and reactivity of a stable, neutral Cu(III) complex.
  • To investigate the reductive elimination pathway from this novel Cu(III) complex for C-C bond formation.

Main Methods:

  • Isolation and characterization of a five-coordinate, neutral square pyramidal Cu(III) complex.
  • Quantitative yield determination of the reductive elimination product (CH3-CF3).
  • Mechanistic studies to elucidate the reaction pathway.

Main Results:

  • Successfully isolated a stable, five-coordinate, neutral square pyramidal Cu(III) complex.
  • The Cu(III) complex underwent reductive elimination to yield CH3-CF3 in quantitative yield.
  • Mechanistic studies indicated a synchronous bond-breaking/bond-forming process via a three-membered ring transition state.

Conclusions:

  • Demonstrated the feasibility of reductive elimination from a neutral Cu(III) complex.
  • Established a new synthetic route for C-C bond formation using copper catalysis.
  • Provided mechanistic insight into the reductive elimination process involving a three-membered ring transition state.