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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.

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...

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

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.

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.
The hydrogenation process takes place on the...

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation

Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...

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Related Experiment Video

Updated: Dec 6, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

Mechanochemical Solvent-Free Catalytic C-H Methylation.

Shengjun Ni¹, Matic Hribersek¹, Swarna K Baddigam¹

¹Department of Chemistry-BMC, Uppsala University, Box 576, 75123, Uppsala, Sweden.

Angewandte Chemie (International Ed. in English)

|October 8, 2020

Summary

Mechanochemical C-H methylation offers a solvent-free, highly regioselective method for modifying arenes. This efficient technique works for late-stage functionalization of bioactive molecules and simplifies organometallic complex synthesis.

Keywords:

C−H functionalization arenes mechanochemistry organometallics rhodium

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Published on: June 24, 2022

Area of Science:

Organic Chemistry
Organometallic Chemistry
Green Chemistry

Background:

C-H methylation is a crucial transformation in organic synthesis.
Traditional methods often require harsh conditions, solvents, and exhibit limited functional group tolerance.
Developing efficient and sustainable C-H functionalization strategies is an ongoing challenge.

Purpose of the Study:

To report a novel mechanochemical, solvent-free method for C-H methylation of (hetero)arenes.
To demonstrate the utility of this method for late-stage functionalization of biologically active compounds.
To showcase the application of mechanochemistry in synthesizing challenging organometallic complexes.

Main Methods:

Rhodium-catalyzed C-H methylation utilizing ball milling (mechanochemistry).
Solvent-free reaction conditions.
Regioselective methylation of aromatic and heteroaromatic compounds.

Main Results:

Achieved highly regioselective C-H methylation of (hetero)arenes under solvent-free conditions.
Demonstrated excellent functional group compatibility, including late-stage methylation of bioactive molecules.
Observed significantly shorter reaction times compared to solution-based methods without external heating.
Successfully synthesized organometallic complexes that are difficult to prepare conventionally.

Conclusions:

Mechanochemical C-H methylation provides a sustainable and efficient alternative to traditional solution-based methods.
The developed protocol offers broad applicability in late-stage functionalization and organometallic synthesis.
This solvent-free approach aligns with green chemistry principles, reducing waste and energy consumption.