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Related Concept Videos

Catalysis02:50

Catalysis

27.2K
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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.4K
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...
3.4K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.9K
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.
7.9K
Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

5.6K
Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.
5.6K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.7K
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.
10.7K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.2K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.2K

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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

Published on: March 20, 2014

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Organocatalyst based cross-catalytic system.

Marieke J Veenstra1, Syuzanna R Harutyunyan1

  • 1Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, Groningen, 9747 AG, The Netherlands. s.harutyunyan@rug.nl.

Chemical Communications (Cambridge, England)
|November 30, 2022
PubMed
Summary

This study introduces a novel organocatalytic system where two reactions, a deprotection and a Mannich reaction, enhance each other's rates. This cross-catalysis was confirmed through kinetic studies and seeding experiments.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Chemical Kinetics

Background:

  • Organocatalysis offers a sustainable alternative to metal catalysis.
  • Cross-catalytic systems, where products of one reaction catalyze another, are complex but efficient.
  • Understanding reaction networks is crucial for designing novel catalytic processes.

Purpose of the Study:

  • To design and investigate a novel cross-catalytic system using organocatalysis.
  • To demonstrate reciprocal rate enhancement between two distinct organic reactions.
  • To elucidate the cross-catalytic mechanism through kinetic analysis.

Main Methods:

  • Development of a two-component reaction system involving Fmoc-protected proline deprotection and a Mannich reaction.
  • Utilizing proline and a tetrahydroisoquinoline derivative as key catalytic species.
  • Conducting detailed kinetic studies and seeding experiments to validate cross-catalysis.

Main Results:

  • Successful implementation of a cross-catalytic organocatalytic system.
  • Demonstration of reciprocal rate enhancement between the deprotection and Mannich reactions.
  • Kinetic data and seeding experiments provide strong evidence for the proposed cross-catalytic network.

Conclusions:

  • The designed system effectively showcases cross-catalysis in organocatalysis.
  • Proline and the tetrahydroisoquinoline product act as mutual catalysts, enhancing reaction rates.
  • This work provides a foundation for developing more sophisticated organocatalytic reaction networks.