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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...

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.

Properties of Organometallic Compounds

Properties of Organometallic Compounds

Organometallic compounds are compounds that contain a carbon–metal bond. Carbon belongs to an organyl group like alkyl, aryl, allyl, or benzyl groups. The metal can be from Group I or Group II of the periodic table, a transition metal, or a semimetal.

Hydrogen Bonds

Hydrogen Bonds

Hydrogen bonds are weak attractions between atoms that have formed other chemical bonds. One of these atoms is electronegative, like oxygen, and has a partial negative charge. The other is a hydrogen atom that has bonded with another electronegative atom and has a partial positive charge.
Hydrogen Bonds Control the World!
Because hydrogen has very weak electronegativity when it binds with a strongly electronegative atom, such as oxygen or nitrogen, electrons in the bond are unequally shared....

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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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.

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.

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Related Experiment Video

Updated: Oct 17, 2025

Preparation of Polyoxometalate-based Photo-responsive Membranes for the Photo-activation of Manganese Oxide Catalysts

Preparation of Polyoxometalate-based Photo-responsive Membranes for the Photo-activation of Manganese Oxide Catalysts

Published on: August 7, 2018

Organo-Polyoxometalate-Based Hydrogen-Bond Catalysis.

Debora Vilona^1,2,3, Moreno Lelli^2,4, Elise Dumont³

¹Univ Lyon, Université Claude Bernard Lyon 1, CNRS, CNES, ArianeGroup, LHCEP, Bât. Raulin, 2 rue Victor Grignard, 69622, Villeurbanne, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)

|October 13, 2021

Summary

Researchers developed novel urea-inserted organo-polyoxometalates (POMs) that activate urea for hydrogen-bond catalysis in Friedel-Crafts reactions. These POMs show potential for efficient organic synthesis.

Keywords:

cooperative effects hydrogen bonds organic-inorganic hybrid composites organocatalysis polyoxometalates

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Last Updated: Oct 17, 2025

Preparation of Polyoxometalate-based Photo-responsive Membranes for the Photo-activation of Manganese Oxide Catalysts

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Published on: August 7, 2018

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Developing Photosensitizer-Cobaloxime Hybrids for Solar-Driven H2 Production in Aqueous Aerobic Conditions

Published on: October 5, 2019

Area of Science:

Inorganic Chemistry
Catalysis
Materials Science

Background:

Polyoxometalates (POMs) are versatile inorganic clusters with tunable properties.
Organo-polyoxometalates incorporate organic functionalities into POM frameworks.
Hydrogen-bond catalysis is a key strategy in organic synthesis for activating substrates.

Purpose of the Study:

To synthesize novel urea-inserted organo-polyoxometalates (POMs) from a polyoxotungstovanadate precursor.
To investigate the catalytic activity of these modified POMs in hydrogen-bond catalysis.
To elucidate the structural and mechanistic aspects of the catalytic process.

Main Methods:

Preparation and characterization of urea-inserted organo-polyoxometalates.
Application of the synthesized POMs as catalysts in the Friedel-Crafts arylation of trans-β-nitrostyrene.
Computational modeling to determine the stable and catalytically active conformations of the organo-POMs.

Main Results:

Successful synthesis of several urea-inserted organo-polyoxometalates derived from [P₂ V₃ W₁₅ O₆₁ ]^9-.
Demonstrated activation of urea towards hydrogen-bond catalysis, evidenced by the Friedel-Crafts arylation reaction.
Computational studies revealed a stable cis-trans conformation, with an accessible catalytically active trans-trans form at room temperature.

Conclusions:

Urea insertion into the polyoxometallic framework effectively activates urea for hydrogen-bond catalysis.
The organo-POMs are efficient catalysts for the Friedel-Crafts arylation of trans-β-nitrostyrene.
Vanadium-oxo substituents may play a role in nucleophile activation through hydrogen bonding.