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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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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.
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One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

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Updated: Jul 18, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

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Recent Advances in C-H Functionalisation through Indirect Hydrogen Atom Transfer.

Filip S Meger¹, John A Murphy²

¹Institute of Chemical Research of Catalonia (ICIQ), The Barcelona Institute of Science and Technology, 16 Avinguda dels Països Catalans, 43007 Tarragona, Catalonia, Spain.

Molecules (Basel, Switzerland)

|August 26, 2023

Summary

Hydrogen atom transfer (HAT) enables C-H bond functionalization. Recent advances in photoredox catalysis and electrochemistry have significantly expanded HAT

Keywords:

catalysis electrochemistry functionalisation hydrogen atom transfer photoredox radicals

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Area of Science:

Synthetic organic chemistry
Catalysis
Methodology development

Background:

C-H bond functionalization is crucial for synthetic chemistry, offering new retrosynthetic pathways.
Hydrogen atom transfer (HAT) is a key mechanism for generating alkyl radicals from C-H bonds.
Traditional HAT reactions include Barton nitrite ester and Hofmann-Löffler-Freytag reactions.

Purpose of the Study:

To review recent advancements in indirect Hydrogen atom transfer (HAT) for C-H, Si-H, and Ge-H bond functionalization.
To critically discuss new HAT reagents, mechanistic insights, substrate scopes, and contextual background from 2018-2023.

Main Methods:

Review and critical analysis of literature published between 2018 and 2023.
Focus on indirect HAT methodologies, particularly those employing photoredox catalysis and electrochemistry.
Discussion of strategies for achieving site-selectivity in HAT reactions.

Main Results:

Photoredox catalysis and electrochemistry have emerged as powerful tools for HAT-mediated C-H functionalization.
Development of new HAT reagents and protocols has broadened the scope of applicable substrates.
Enhanced mechanistic understanding has led to improved site-selective functionalization strategies.

Conclusions:

Indirect HAT, particularly via photoredox catalysis and electrochemistry, represents a significant evolution in C-H functionalization.
Continued research into HAT reagents, mechanisms, and selectivity will further expand its synthetic utility.
The reviewed methods offer versatile approaches for introducing diverse functional groups into C-H, Si-H, and Ge-H bonds.