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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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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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The pinacol and McMurry reactions involve the reductive coupling of ketones or aldehydes. Similarly, the bimolecular reductive coupling of two ester molecules in the presence of sodium metal in an aprotic solvent yields an α-hydroxy ketone product. The α-hydroxy ketone is also called acyloin, so the reaction is referred to as ‘acyloin condensation.’
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

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By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
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Ethers from Alcohols: Alcohol Dehydration and Williamson Ether Synthesis02:29

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Overview
Ethers can be prepared from organic compounds by various methods. Some of them are discussed below,
Preparation of Ethers by Alcohol Dehydration
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Reductive Etherification via Anion-Binding Catalysis.

Chenfei Zhao1, Christopher A Sojdak1, Wazo Myint1

  • 1Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey , Piscataway, New Jersey 08854, United States.

Journal of the American Chemical Society
|July 26, 2017
PubMed
Summary
This summary is machine-generated.

A new thiourea organocatalyst enables reductive ether synthesis from alcohols and aldehydes/ketones using a simple siloxane reducing agent. This method offers broad substrate scope and functional group tolerance, suppressing unwanted side reactions for efficient ether production.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Ether synthesis is crucial in organic chemistry.
  • Existing methods often require harsh conditions or specialized reagents.
  • Development of efficient and selective catalytic systems is needed.

Purpose of the Study:

  • To develop a novel organocatalytic method for reductive ether synthesis.
  • To utilize readily accessible catalysts and reagents.
  • To achieve high efficiency and selectivity for challenging substrates.

Main Methods:

  • Reductive condensation of alcohols with aldehydes or ketones.
  • Catalysis using a thiourea organocatalyst and hydrochloric acid (HCl).
  • Employing 1,1,3,3-tetramethyldisiloxane as the reducing agent.

Main Results:

  • Successful synthesis of ethers via reductive condensation.
  • Demonstrated applicability to challenging substrate combinations.
  • Exhibited excellent functional group tolerance.
  • Suppressed competing reductive homocoupling of carbonyl compounds.

Conclusions:

  • A practical and efficient organocatalytic system for ether synthesis has been established.
  • The method provides a valuable alternative to existing synthetic routes.
  • The catalyst and conditions are robust and versatile for various applications.