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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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 Alkenes: Catalytic Hydrogenation

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.
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Catalysis

Catalysis

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.

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.

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Photochemical Electrocyclic Reactions: Stereochemistry

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The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

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Dirhodium-Based Supramolecular Framework Catalyst for Visible-Light-Driven Hydrogen Evolution.

Pondchanok Chinapang¹, Hikaru Iwami², Takafumi Enomoto¹

¹Institute for Molecular Science, 5-1 Higashiyama, Myodaiji, Okazaki, Aichi 444-8787, Japan.

Inorganic Chemistry

|July 16, 2021

Summary

This summary is machine-generated.

Researchers developed a novel dirhodium-complex framework for efficient solar-driven hydrogen fuel production. This supramolecular catalyst, utilizing boron dipyrromethene (BDP) moieties with heavy atoms, shows high performance and durability.

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Area of Science:

Materials Science
Photocatalysis
Renewable Energy

Background:

Addressing global energy demands and environmental issues necessitates alternatives to fossil fuels.
Direct solar energy conversion into clean fuels is a promising strategy.
Developing efficient photocatalysts for hydrogen evolution is crucial.

Purpose of the Study:

To design and synthesize novel dirhodium-complex-based supramolecular framework catalysts for visible-light-driven hydrogen evolution.
To investigate the role of boron dipyrromethene (BDP) moieties and heavy atoms in photocatalytic activity.
To evaluate the performance, durability, and reusability of the developed catalyst.

Main Methods:

Synthesis of two dirhodium complexes functionalized with visible-light-harvesting BODIPY (BDP) moieties.
Self-assembly of complexes into supramolecular framework catalysts stabilized by noncovalent interactions.
Photocatalytic hydrogen evolution experiments under visible light irradiation.
Analysis of the effect of heavy atoms on catalytic activity and mechanistic studies.

Main Results:

Supramolecular framework catalysts retained the visible-light-harvesting properties of BDP moieties.
The catalyst incorporating heavy atoms in BDP moieties demonstrated significant hydrogen evolution (275.8 μmol g⁻¹ h⁻¹).
The catalyst without heavy atoms was inactive, highlighting the importance of heavy atoms for activity.

Conclusions:

A novel dirhodium-complex-based supramolecular framework catalyst was successfully developed for hydrogen evolution.
The presence of heavy atoms in BDP moieties is critical for achieving high photocatalytic activity.
The catalyst exhibits excellent durability, reusability, and facile separation, making it a viable option for clean fuel production.