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Pericyclic Reactions: Introduction

Pericyclic Reactions: Introduction

Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...

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.

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.

Thermal and Photochemical Electrocyclic Reactions: Overview

Thermal and Photochemical Electrocyclic Reactions: Overview

Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.

[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.

Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation

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Related Experiment Video

Updated: Jun 26, 2025

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

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

Published on: March 20, 2014

Deciphering complexity in Pd-catalyzed cross-couplings.

George E Clarke¹, James D Firth¹, Lyndsay A Ledingham¹

¹Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.

Nature Communications

|May 10, 2024

Summary

This summary is machine-generated.

This study introduces a high-throughput method to analyze complex palladium-catalyzed reactions. It reveals how solvents and conditions influence product distribution, aiding chemical discovery.

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

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Scaled-Up Preparation of an Intermediate of Upatinib, ACT051-3

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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

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

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Published on: April 4, 2014

Scaled-Up Preparation of an Intermediate of Upatinib, ACT051-3

Scaled-Up Preparation of an Intermediate of Upatinib, ACT051-3

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Area of Science:

* Organic Chemistry
* Catalysis
* Chemical Data Analysis

Background:

* Understanding complex chemical reactions is crucial for advancing synthetic chemistry and mechanistic studies.
* Analyzing the complete product profile, not just the desired product, provides deeper insights into reaction pathways.
* Palladium-catalyzed reactions are widely used but can be mechanistically complex.

Purpose of the Study:

* To develop and apply a high-throughput experimentation and multivariate data analysis methodology.
* To comprehensively examine the reaction signature of a complex palladium-catalyzed process.
* To identify factors influencing product distribution and side-product formation.

Main Methods:

* High-throughput experimentation was employed to systematically vary reaction conditions.
* Multivariate data analysis techniques, including Principal Component Analysis (PCA), Correspondence Analysis, and hierarchical clustering with heatmaps, were utilized.
* A model palladium-catalyzed reaction involving 2-bromo-N-phenylbenzamide was studied across eight solvents, four reaction times, and five temperatures.

Main Results:

* The methodology successfully elucidated the full reaction signature of a complex palladium-catalyzed system.
* Multivariate analysis identified key factors contributing to variance in product distributions.
* Significant associations were found between specific solvents and the formation of various reaction products, including a dominant N-phenyl phenanthridinone and numerous side products.

Conclusions:

* The developed methodology provides a powerful approach for dissecting complex catalytic reactions.
* Understanding the interplay between reaction conditions (solvents, temperature, time) and product profiles is essential for mechanistic elucidation.
* This approach accelerates discovery chemistry by enabling efficient exploration of reaction landscapes and identification of side-product correlations.