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Radical Anti-Markovnikov Addition to Alkenes: Mechanism

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The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...

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.

Radical Anti-Markovnikov Addition to Alkenes: Thermodynamics

Radical Anti-Markovnikov Addition to Alkenes: Thermodynamics

The anti-Markovnikov addition of hydrogen halides to an alkene is thermodynamically feasible only with HBr. The radical addition reaction with other hydrogen halides like HCl and HI is thermodynamically unfavorable.

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.

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Related Experiment Video

Updated: Feb 14, 2026

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions

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Published on: March 20, 2014

Palladium-catalysed anti-Markovnikov selective oxidative amination.

Daniel G Kohler¹, Samuel N Gockel¹, Jennifer L Kennemur¹

¹Department of Chemistry, University of Illinois, Urbana-Champaign, 600 S. Mathews, Urbana, Illinois 61801, USA.

Nature Chemistry

|February 21, 2018

Summary

Researchers developed a new palladium-catalyzed oxidative amination for synthesizing nitrogen-containing compounds. This efficient method achieves anti-Markovnikov selectivity, offering a general approach from readily available starting materials.

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Published on: August 18, 2020

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Nitrogen-containing compounds are crucial in biologically active molecules.
Existing synthetic methods are often inefficient and lack functional group tolerance.
A general and efficient synthesis of nitrogen-containing compounds is highly desirable.

Purpose of the Study:

To develop a novel palladium-catalyzed oxidative amination reaction.
To achieve anti-Markovnikov selectivity in nitrogen addition to alkenes.
To provide a general and efficient method for synthesizing nitrogen-containing compounds.

Main Methods:

Palladium-catalyzed oxidative amination of alkenes with imides.
Utilizing a palladate catalyst for trans-aminopalladation.
Investigating reaction scope and mechanistic pathways.

Main Results:

Successful synthesis of terminal imides via anti-Markovnikov addition.
Demonstration of olefin isomerization to thermodynamically favored products.
Comprehensive scope and mechanistic studies reported.

Conclusions:

The developed method offers an efficient and general approach to nitrogen-containing compounds.
The reaction proceeds with high anti-Markovnikov selectivity.
This work advances synthetic strategies for accessing valuable nitrogen motifs.