Related Experiment Video
Updated: Aug 12, 2025

Atom Transfer Radical Polymerization of Functionalized Vinyl Monomers Using Perylene as a Visible Light Photocatalyst
Published on: April 22, 2016
Visible-Light Promoted Intramolecular para-Cycloadditions on Simple Aromatics
Maurizio Chiminelli1, Andrea Serafino1, Davide Ruggeri1
1Department of Chemistry, Life Sciences and Environmental Sustainability, Università di Parma, Parco Area delle Scienze 17/A, 43 124, Parma, Italy.
Abstract:
Dearomative cycloadditions are a powerful tool to access a large chemical space exploiting simple and ubiquitous building blocks. The energetic burden due to the loss of aromaticity has however greatly limited their synthetic potential. We devised a general intramolecular method that overcomes these limitations thanks to the photosensitization of allenamides. The visible-light-promoted process gives complex [2.2.2]-(hetero)-bicyclooctadienes at room temperature, likely through the stabilization of transient (bi)radicals by naphthalene. The reaction tolerates several valuable functionalities, offering a convenient handle for a myriad of applications, including original isoindoles and metal complexes.
More Related Videos
07:12Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
12:07Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
Published on: April 1, 2013
Related Concept Videos
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cycloaddition Reactions: Overview
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Nucleophilic Aromatic Substitution: Elimination–Addition