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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...
Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction01:09

Aldehydes and Ketones to Alkanes: Wolff–Kishner Reduction

Wolff–Kishner reduction involves converting aldehydes and ketones to alkanes using hydrazine and a base. The reaction converts a carbonyl group to a methylene group. The method was independently discovered by N. Kishner in 1911 and L. Wolff in 1912. The reduction is carried out in high-boiling solvents such as ethylene glycol and diethylene glycol because heat is required to deprotonate the N–H proton in one of the reaction steps.
Alcohols from Carbonyl Compounds: Reduction02:23

Alcohols from Carbonyl Compounds: Reduction

Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...

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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
13:09

Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations

Published on: January 4, 2018

Hydrogen-free alkene reduction in continuous flow.

Andrew S Kleinke1, Timothy F Jamison

  • 1Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Organic Letters
|January 24, 2013
PubMed
Summary
This summary is machine-generated.

This study introduces a novel continuous hydrogenation method that avoids hydrogen gas and metal catalysts. It efficiently generates diimide using a unique reagent combination in a flow reactor for faster reactions.

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

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Utilization of Stop-flow Micro-tubing Reactors for the Development of Organic Transformations
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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid

Published on: November 15, 2017

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Chemical Engineering

Background:

  • Continuous hydrogenation processes traditionally rely on hydrogen gas (H2) and metal catalysts.
  • Developing alternative, safer, and more efficient hydrogenation methods is crucial for sustainable chemistry.
  • Diimide is a valuable but often challenging intermediate to generate and utilize in organic synthesis.

Purpose of the Study:

  • To develop the first continuous hydrogenation method that does not require hydrogen gas or metal catalysis.
  • To establish a novel reagent combination for the in-situ generation of diimide.
  • To optimize the process using a simple flow reactor for enhanced efficiency and safety.

Main Methods:

  • Utilized a novel combination of reagents for diimide generation.
  • Employed a simple flow reactor system for continuous processing.
  • Operated the reactor at elevated temperatures to minimize residence time.

Main Results:

  • Successfully demonstrated continuous diimide generation without H2 or metal catalysts.
  • The flow reactor enabled safe operation at elevated temperatures.
  • Minimized reaction residence times, leading to improved process efficiency.

Conclusions:

  • This work presents a groundbreaking approach to continuous hydrogenation.
  • The developed method offers a safer and potentially more economical alternative for diimide synthesis.
  • The use of flow chemistry enhances the practicality and scalability of this novel hydrogenation technique.