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Related Concept Videos

Catalysis02:50

Catalysis

31.2K
The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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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

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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.
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Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...
9.6K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
13.2K
Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration02:35

Ethers from Alkenes: Alcohol Addition and Alkoxymercuration-Demercuration

9.1K
Overview
Ethers can also be prepared from alkenes through acid-catalyzed addition of alcohols and alkoxymercuration–demercuration.
Preparation of Ethers by Acid-Catalyzed Addition of Alcohol to Alkenes
The acid-catalyzed addition of alcohol to an alkene involves treating the alkene with an excess of alcohol in the presence of an acid catalyst to form an ether under suitable conditions. The hydrogen will add to the less substituted carbon so that the nucleophile can attack the more substituted...
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Deoxygenation of Ethers To Form Carbon-Carbon Bonds via Nickel Catalysis.

Zhi-Chao Cao1, Zhang-Jie Shi1,2,3

  • 1College of Chemistry and Molecular Engineering, Peking University , Beijing 100871, China.

Journal of the American Chemical Society
|April 27, 2017
PubMed
Summary
This summary is machine-generated.

Researchers developed a nickel-catalyzed method to form carbon-carbon bonds by removing oxygen from ethers. This efficient process creates sp3-sp3 carbon-carbon bonds with broad functional group tolerance.

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Area of Science:

  • Organic Chemistry
  • Catalysis

Background:

  • Carbon-carbon bond formation is crucial in organic synthesis.
  • Ether cleavage typically requires harsh conditions or specific functional groups.

Purpose of the Study:

  • To develop an efficient and economical method for constructing sp3-sp3 carbon-carbon bonds.
  • To achieve dual carbon-oxygen bond activation in ethers using nickel catalysis.

Main Methods:

  • Nickel-catalyzed reaction utilizing reductants.
  • Extrusion of the oxygen atom from ether substrates.
  • Dual C-O activation strategy.

Main Results:

  • Successful construction of carbon-carbon bonds via ether O-atom extrusion.
  • Demonstrated good functional group tolerance.
  • Established a highly economic synthetic route.

Conclusions:

  • The developed protocol offers a novel and efficient pathway for sp3-sp3 C-C bond formation.
  • This nickel-catalyzed dual C-O activation of ethers is a valuable addition to synthetic organic chemistry.