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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 Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

Radical Anti-Markovnikov Addition to Alkenes: Overview

Radical Anti-Markovnikov Addition to Alkenes: Overview

The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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.

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

Introduction
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.

Acidity of 1-Alkynes

Acidity of 1-Alkynes

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.

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Related Experiment Video

Updated: Jul 9, 2025

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

Recent Advances in Asymmetric Catalysis Using p-Block Elements.

Milan Pramanik¹, Michael G Guerzoni¹, Emma Richards¹

¹Cardiff Catalysis Institute, School of Chemistry, Cardiff University, Translational Research Hub, Maindy Road, Cathays, Cardiff, CF24 4HQ, Cymru/Wales, UK.

Angewandte Chemie (International Ed. in English)

|December 1, 2023

Summary

This summary is machine-generated.

Chiral p-block element catalysts offer a sustainable approach to enantioselective synthesis. These main group catalysts provide high selectivity and reactivity for generating valuable chiral molecules.

Keywords:

Aluminium Bismuth Boron Enantioselective Catalysis Frustrated Lewis Pairs

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Area of Science:

Organic Chemistry
Asymmetric Catalysis
Main Group Chemistry

Background:

Enantioselective reactions creating stereogenic centers are crucial in organic synthesis.
Traditional methods rely on metal catalysts with chiral ligands or chiral organocatalysts.
A need exists for complementary, sustainable catalytic approaches.

Purpose of the Study:

To review recent advancements in main group catalysis for enantioselective reactions.
To highlight the use of p-block elements (boron, aluminum, phosphorus, bismuth) as catalysts.
To showcase these catalysts as a sustainable alternative for generating chiral molecules.

Main Methods:

Focus on catalytic systems utilizing chiral p-block elements.
Review of literature on enantioselective transformations mediated by these main group catalysts.
Emphasis on catalysts derived from boron, aluminum, phosphorus, and bismuth.

Main Results:

Chiral p-block element catalysts demonstrate high selectivity and excellent reactivity.
These catalysts are often abundant, less toxic, and cost-effective.
Successful application in various asymmetric reactions for synthesizing value-added compounds.

Conclusions:

Main group catalysis using p-block elements is a viable and sustainable strategy for enantioselective synthesis.
These catalysts offer significant advantages in terms of efficiency, selectivity, and environmental impact.
The findings support the broader adoption of these sustainable methods in organic synthesis.