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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...

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.

Hydroboration-Oxidation of Alkenes

Hydroboration-Oxidation of Alkenes

In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.

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.

Preparation of Alcohols via Addition Reactions

Preparation of Alcohols via Addition Reactions

Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...

Radical Oxidation of Allylic and Benzylic Alcohols

Radical Oxidation of Allylic and Benzylic Alcohols

Activated manganese(IV) oxide can selectively oxidize allylic and benzylic alcohols via a radical intermediate mechanism. Primary allylic alcohols are oxidized to aldehydes, while secondary allylic alcohols yield ketones. The redox reaction of potassium permanganate with an Mn(II) salt such as manganese sulfate (under either alkaline or acidic conditions), followed by thorough drying, yields the oxidizing agent: activated MnO2. While MnO2 is insoluble in the solvents used for the reaction, the...

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Related Experiment Video

Updated: Jan 7, 2026

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

Coordinatively Unsaturated IrC₃ Single-Atom Catalysts for Efficient Methanol Oxidation Reaction.

Liyuan Gong^1,2, Yabin Xu¹, Shurui Gao³

¹State Key Laboratory of Chemo/Bio-Sensing and Chemometrics, College of Chemistry and Chemical Engineering, the National Supercomputer Centers in Changsha, Advanced Catalytic Engineering Research Center of the Ministry of Education, Hunan University, Changsha, China.

Advanced Materials (Deerfield Beach, Fla.)

|December 26, 2025

Summary

A novel single iridium (Ir) atom catalyst with IrC3 sites boosts methanol oxidation reaction (MOR) efficiency at high temperatures. This catalyst enhances methanol adsorption and facilitates CO oxidation, overcoming key kinetic limitations for hydrogen production.

Keywords:

H2 production adsorption energy coordinatively unsaturated sites methanol oxidation reaction

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Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

Published on: April 10, 2018

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Last Updated: Jan 7, 2026

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Heterogeneous Removal of Water-Soluble Ruthenium Olefin Metathesis Catalyst from Aqueous Media Via Host-Guest Interaction

Published on: August 23, 2018

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

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

Synthesis and Performance Characterizations of Transition Metal Single Atom Catalyst for Electrochemical CO2 Reduction

Published on: April 10, 2018

Area of Science:

Electrochemistry
Catalysis
Renewable Energy

Background:

Methanol oxidation reaction (MOR) is vital for energy conversion but hindered by slow kinetics, particularly CO oxidation.
Strong CO adsorption and limited hydroxyl (OH) species at active sites impede MOR efficiency.

Purpose of the Study:

To develop a single Ir atom catalyst with IrC3 sites for efficient electrocatalysis of MOR at elevated temperatures.
To address the challenge of CO poisoning and insufficient OH species in MOR.

Main Methods:

Development of single Ir atom catalysts featuring coordinatively unsaturated IrC3 sites.
Electrocatalysis of MOR under elevated temperatures using a high-temperature polymer electrolyte membrane electrolyzer (HT-PEME).
Analysis of methanol and CO adsorption energies and electrochemical water dissociation.

Main Results:

The IrC3 sites exhibit stronger methanol adsorption and weaker CO adsorption, breaking the scaling relationship.
Accelerated electrochemical water dissociation by IrC3 and IrC4 sites generates abundant *OH species.
The catalyst achieved an onset potential of 0.05 V and a high H2 generation rate (8694 molH2 molIr-1 h-1) at 180°C.

Conclusions:

The developed IrC3 single atom catalyst significantly enhances MOR kinetics by balancing adsorption energies and providing ample *OH species.
This catalyst demonstrates superior performance compared to conventional Ir-C and Pt/C catalysts in HT-PEME.
The findings offer a promising strategy for efficient hydrogen utilization via MOR.