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Related Concept Videos

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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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C–C Bond Formation: Aldol Condensation Overview01:10

C–C Bond Formation: Aldol Condensation Overview

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Aldol condensation is an important route in synthetic organic chemistry used to generate a new carbon–carbon bond under basic or acidic conditions. The aldol condensation reaction presented in Figure 1 constitutes an aldol addition reaction followed by the dehydration process.
17.9K
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene01:11

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The Friedel–Crafts acylation reactions involve the addition of an acyl group to an aromatic ring. These reactions proceed via electrophilic aromatic substitution by employing an acyl chloride and a Lewis acid catalyst such as aluminum chloride to form aryl ketone.
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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Ag-catalyzed C-H/C-C bond functionalization.

Qing-Zhong Zheng1, Ning Jiao

  • 1Department of Chemistry and State Key Laboratory Cultivation Base of Natural Gas Conversion, School of Chemistry and Chemical Engineering, Ningxia University, Yinchuan 750021, China.

Chemical Society Reviews
|April 9, 2016
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Silver catalysis is rapidly advancing in organic chemistry. This review focuses on silver(i)-catalyzed C-H/C-C bond functionalization, highlighting its versatility and mechanisms.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Organometallic Chemistry

Background:

  • Silver, a coinage metal, has a long history of use.
  • Silver catalysis has emerged as a frontier area in organic chemistry.
  • Silver(i) is increasingly recognized as a versatile catalyst for organic transformations.

Purpose of the Study:

  • To provide a systematic review of silver-catalyzed C-H/C-C bond functionalization.
  • To consolidate recent advancements in this field.
  • To elucidate the mechanisms underlying these transformations.

Main Methods:

  • Literature review of silver-catalyzed reactions.
  • Analysis of reaction mechanisms.
  • Focus on C-H/C-C bond functionalization.

Main Results:

  • Silver(i) catalysis has shown significant improvements in recent years.
  • Silver is a versatile catalyst for various organic transformations.
  • No prior systematic review on Ag-catalyzed C-H/C-C bond functionalization exists.

Conclusions:

  • Silver catalysis, particularly Ag(i), is a powerful tool for C-H/C-C bond functionalization.
  • Further research is warranted to fully understand and exploit silver's catalytic potential.
  • This review serves as a comprehensive resource for the field.