Related Experiment Video
Updated: Jun 25, 2025
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Cascade Radical Pathway-Enabled Nitrogen-Sulfur Coupling: Access to Isothiazolo[3,4-b]-meso-tetraarylporphyrins
Abhijeet Singh1, Mahendra Nath1
1Department of Chemistry, Faculty of Science, University of Delhi, Delhi 110 007, India.
Abstract:
A catalyst-free radical-mediated domino strategy for the construction of isothiazolo[3,4-b]-meso-tetraarylporphyrins was developed. During the course of the reaction, 2-benzothioylamino-3-thioformyl-meso-tetraarylporphyrins generated in situ after the addition of Lawesson's reagent to a solution of 2-benzoylamino-3-formyl-meso-tetraarylporphyrins in refluxing toluene underwent a homolytic cleavage to produce nitrogen-sulfur radicals. Subsequently, the formation of a new N-S bond through an intramolecular cascade radical coupling provided direct access to novel β-isothiazole-fused porphyrins.
More Related Videos
Related Concept Videos
Radical Reactivity: Overview
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Radical Reactivity: Nucleophilic Radicals
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism
![[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F59739.jpg&w=3840&q=50)
