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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

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.

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.

Electrophilic Aromatic Substitution: Overview

Electrophilic Aromatic Substitution: Overview

In an electrophilic aromatic substitution reaction, an electrophile substitutes for a hydrogen of an aromatic compound.

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.

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...

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

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Published on: April 4, 2014

Cathodic Aromatic C,C Cross-Coupling Reaction via Single Electron Transfer Pathway.

Yang Qu¹, Hiroyuki Tateno², Yoshimasa Matsumura³

¹Graduate School of Environment and Information Sciences, Yokohama National University, 79-7, Tokiwadai, Hodogaya-ku, Yokohama 240851, Japan. qu-yang-rv@ynu.jp.

Molecules (Basel, Switzerland)

|March 9, 2017

Summary

This study introduces a new cathodic cross-coupling reaction for aryl halides and arenes. This metal-free method uses a single electron transfer mechanism under mild conditions, avoiding harsh reagents.

Keywords:

C,C cross-coupling electrochemical synthesis single electron transfer

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Published on: April 1, 2013

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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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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

Published on: April 1, 2013

Area of Science:

Organic Chemistry
Electrochemistry

Background:

Transition metal catalysts are commonly used in cross-coupling reactions.
These reactions often require harsh conditions or expensive reagents.

Purpose of the Study:

To develop a novel, metal-free cross-coupling reaction.
To utilize a cathodic single electron transfer (SET) mechanism for aryl halide activation.

Main Methods:

Development of a cathodic cross-coupling reaction.
Activation of aryl halides via single electron transfer (SET) from a cathode.
Radical chain mechanism involving anion radical intermediates.

Main Results:

Successful cross-coupling of aryl halides with arenes.
Demonstration of a metal-free and single electron donor-free reaction.
Reaction proceeds under mild conditions.

Conclusions:

A novel and efficient cathodic cross-coupling reaction has been established.
The SET mechanism provides a viable alternative to traditional cross-coupling methods.
This approach offers a greener and milder synthetic route.