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Preparation of Diols and Pinacol Rearrangement

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

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

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

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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.

Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

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Diels–Alder reactions between cyclic dienes locked in an s-cis configuration and dienophiles yield bridged bicyclic products.

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.

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.

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Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst

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Photoinduced Vinylogous Dearomatization.

Xinxin Lv¹, Ya-Nan Qi¹, Jiahao Wang¹

¹NMPA Key Laboratory for Research and Evaluation of Innovative Drug, School of Chemistry and Chemical Engineering, Henan Normal University; Pingyuan Laboratory, Xinxiang 453007, Henan, P. R. China.

Organic Letters

|April 25, 2023

Summary

Researchers developed a novel photoinduced vinylogous dearomatization. This efficient reaction synthesizes valuable pharmaceutical compounds, including chromones and dihydrobenzothiophenes, from benzothiophenes and methylenechromanones.

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Published on: November 21, 2017

Area of Science:

Organic Chemistry
Photochemistry
Medicinal Chemistry

Background:

Vinylogous dearomatization is a key transformation for constructing complex organic molecules.
Benzothiophenes and chromones are prevalent scaffolds in pharmaceutically active compounds.
Developing efficient synthetic routes to access these structures is of significant interest.

Purpose of the Study:

To report the first example of vinylogous dearomatization involving benzothiophenes.
To develop a photoinduced synthetic strategy for accessing valuable pharmaceutical building blocks.
To explore the reaction scope and mechanism of this novel transformation.

Main Methods:

Utilized a photoinduced platform for the reaction.
Employed functionalized benzothiophenes and 3-methylenechroman-4-ones as starting materials.
Investigated reaction intermediates and mechanistic pathways, including hydrogen-atom transfer and radical coupling.

Main Results:

Achieved efficient synthesis of diverse products containing both chromone and 2,3-dihydrobenzo[b]thiophene moieties.
Demonstrated the utility of the developed method for constructing complex molecular architectures.
Elucidated the reaction mechanism involving key steps like dearomatization and radical cross-coupling.

Conclusions:

Successfully established the first vinylogous dearomatization of benzothiophenes.
The photoinduced method provides a facile route to pharmaceutically relevant chromones and dihydrobenzothiophenes.
This work expands the synthetic toolbox for accessing valuable heterocyclic compounds.