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Halogenation of Alkenes

Halogenation of Alkenes

Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.

Cycloaddition Reactions: Overview

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).

Radical Substitution: Allylic Bromination

Radical Substitution: Allylic Bromination

In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...

Electrophilic 1,2- and 1,4-Addition of X2 to 1,3-Butadiene

Electrophilic 1,2- and 1,4-Addition of X₂ to 1,3-Butadiene

Electrophilic addition of halogens to alkenes proceeds via a cyclic halonium ion to form a 1,2-dihalide or a vicinal dihalide.

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.

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Tandem radical cyclization to construct poly-brominated 2-oxindoles.

Fengjuan Chen¹, Yajun Wang, Shijun Zhao

¹College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China. huocongde1978@hotmail.com.

Organic & Biomolecular Chemistry

|September 7, 2017

Summary

A new metal-free method uses tert-butyl hydroperoxide (TBHP) to tribromomethylate alkenes. This approach efficiently synthesizes tribromomethylated 2-oxindoles using air as an oxidant.

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Area of Science:

Organic Chemistry
Synthetic Chemistry
Radical Chemistry

Background:

Tribromomethylation is a valuable synthetic transformation.
Existing methods often require metal catalysts or harsh conditions.
Developing metal-free, aerobic methods is highly desirable.

Purpose of the Study:

To develop a novel metal-free protocol for the tribromomethylation of activated alkenes.
To synthesize tribromomethylated 2-oxindoles using readily available starting materials.
To utilize air as a sustainable terminal oxidant.

Main Methods:

Catalytic amounts of tert-butyl hydroperoxide (TBHP) were employed.
The reaction involved N-arylacrylamides and carbon tetrabromide (CBr4).
A tandem radical cyclization process was proposed.

Main Results:

Efficient metal-free aerobic tribromomethylation of activated alkenes was achieved.
Tribromomethylated 2-oxindoles were successfully synthesized.
1,1-dibromoolefin derivatives were formed under neat conditions at higher temperatures.

Conclusions:

A novel, efficient, and metal-free aerobic method for tribromomethylation has been established.
The developed protocol offers a sustainable route to valuable tribromomethylated compounds.
The reaction conditions can be tuned to yield different product classes.