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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.

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.

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.

Preparation and Reactions of Sulfides

Preparation and Reactions of Sulfides

Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.

Cycloaddition Reactions: MO Requirements for Thermal Activation

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.

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.

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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

Silacyclization through palladium-catalyzed intermolecular silicon-based C(sp²)-C(sp³) cross-coupling.

Ying Qin¹, Lianghui Li¹, Jin-Yuan Liang¹

¹State Key Laboratory and Institute of Elemento-Organic Chemistry, Frontiers Science Center for New Organic Matter, College of Chemistry, Nankai University Tianjin 300071 China dongbing.chem@nankai.edu.cn.

Chemical Science

|November 11, 2021

Summary

This study introduces a novel palladium-catalyzed silicon-based cross-coupling reaction for synthesizing sila-benzo[b]oxepines. This efficient ring expansion strategy offers a new route for creating complex silicon-containing heterocyclic compounds.

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Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Area of Science:

Organosilicon Chemistry
Synthetic Organic Chemistry
Catalysis

Background:

Silicon-based cross-coupling is a reliable method for C-C bond formation.
Its application in silacycle synthesis via ring expansion is underexplored.

Purpose of the Study:

To develop the first intermolecular silacyclization strategy for ring expansion.
To synthesize novel sila-benzo[b]oxepines using palladium catalysis.

Main Methods:

Employing palladium-catalyzed silicon-based C(sp2)-C(sp3) cross-coupling.
Utilizing silacyclobutanes (SCBs) as key building blocks.

Main Results:

Successfully developed an efficient intermolecular silacyclization strategy.
Modularly assembled diverse and novel sila-benzo[b]oxepines.
Demonstrated good functional group tolerance in the reaction.

Conclusions:

The developed method provides a new avenue for silacycle synthesis.
The reaction's success is attributed to silicon's affinity for oxygen and SCB ring strain.
Offers a versatile approach for constructing complex organosilicon heterocycles.