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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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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

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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

2.0K
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.
2.0K
Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.7K
Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
3.7K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

5.1K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
5.1K
Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

7.3K
Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Copper mediated carbometalation reactions.

D S Müller1, I Marek1

  • 1The Mallat Family Laboratory of Organic Chemistry, Schulich Faculty of Chemistry, and The Lise Meitner-Minerva Center for Computational Quantum Chemistry, Technion-Israel Institute of Technology, Technion City, Haifa 32000, Israel. chilanm@tx.technion.ac.il.

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Summary

Carbocupration of alkynes and copper-mediated carbometalation of cyclopropenes are valuable synthetic methods. These reactions offer high selectivity for constructing complex cyclic and acyclic molecules with stereocenters.

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Area of Science:

  • Organic Chemistry
  • Organometallic Chemistry

Background:

  • Carbocupration of alkynes, discovered in the 1970s, offers high selectivity and synthetic value.
  • Copper-mediated carbometalation of cyclopropenes has gained attention for constructing poly-substituted cyclopropanes.

Purpose of the Study:

  • To review the key features of carbocupration of alkynes.
  • To provide a comprehensive overview of copper-mediated carbometalation of cyclopropenes.
  • To highlight the synthetic utility of these reactions in creating complex carbon structures.

Main Methods:

  • Literature review of carbocupration reactions.
  • Comprehensive analysis of copper-mediated carbometalation of cyclopropenes.
  • Discussion of synthetic transformations of resulting cyclopropanes.

Main Results:

  • Carbocupration reactions exhibit exceptional selectivities.
  • Copper-mediated carbometalation enables highly selective synthesis of poly-substituted cyclopropanes.
  • These cyclopropanes can be converted into acyclic compounds with multiple tertiary or quaternary stereocenters.

Conclusions:

  • Carbocupration and copper-mediated carbometalation are powerful tools in organic synthesis.
  • These methods facilitate the stereoselective construction of intricate molecular architectures.
  • The reviewed reactions are crucial for accessing valuable acyclic and cyclic compounds.