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Catalysis02:50

Catalysis

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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

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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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Crossed Aldol Reactions: Overview01:04

Crossed Aldol Reactions: Overview

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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.
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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)00:53

Olefin Metathesis Polymerization: Acyclic Diene Metathesis (ADMET)

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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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General cross-coupling reactions with adaptive dynamic homogeneous catalysis.

Indrajit Ghosh1, Nikita Shlapakov2,3, Tobias A Karl2

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Nature
|June 14, 2023
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Summary

This study introduces adaptive dynamic homogeneous catalysis (AD-HoC) using nickel for versatile C(sp2)-heteroatom cross-coupling reactions. This self-adjusting system simplifies reaction optimization across diverse nucleophiles and bond formations.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Cross-coupling reactions are vital in organic synthesis but often require specific, case-by-case optimization.
  • Existing methods for (het)aryl halide and nucleophile coupling are diverse but lack generality.
  • Variability in reaction conditions necessitates frequent re-optimization for different compound classes.

Purpose of the Study:

  • To develop a general and adaptable catalytic system for C(sp2)-(hetero)atom cross-coupling reactions.
  • To introduce adaptive dynamic homogeneous catalysis (AD-HoC) using nickel under visible-light-driven redox conditions.
  • To simplify the classification and execution of cross-coupling reactions with various nucleophiles.

Main Methods:

  • Utilized nickel-catalyzed adaptive dynamic homogeneous catalysis (AD-HoC).
  • Employed visible-light-driven redox reaction conditions.
  • Demonstrated adaptability by varying nucleophiles and optionally using amine bases.

Main Results:

  • Achieved general C(sp2)-(hetero)atom coupling reactions with a self-adjusting catalytic system.
  • Successfully classified dozens of nucleophile classes for cross-coupling.
  • Synthetically demonstrated nine distinct bond-forming reactions (C-S, C-Se, C-N, C-P, C-B, C-O, C-C, C-Si, C-Cl) with numerous examples.
  • Established predictable reaction conditions adaptable to different nucleophiles.

Conclusions:

  • AD-HoC offers a versatile and predictable platform for a wide range of cross-coupling reactions.
  • The self-adjustive nature of the nickel catalyst simplifies synthetic strategy and optimization.
  • This methodology broadens the scope of efficient C(sp2)-(hetero)atom bond formation in organic synthesis.