Construction of bi(hetero)aryls via dicyanopyrazine-mediated photochemical cross-coupling
Zuzana Burešová1, Veronika Jandová1, Milan Klikar1
1Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 53210, Czech Republic. filip.bures@upce.cz.
Abstract:
A photochemical cross-coupling protocol towards bi(hetero)aryls has been developed. The coupling reactions were mediated by dicyanopyrazine photoredox catalyst, while a photoinduced disproportionation process has been identified as an accompanying mechanism, especially for pyrrole derivatives. The developed method allows the cross-coupling of five-membered rings such as pyrrole, imidazole, thiazole and oxazole as well as various diazines (pyridine and pyrimidine) and benzene derivatives. A plausible mechanism of the reaction has also been disclosed. The practical application and relevance of the developed method were demonstrated by constructing an atorvastatin core or by the gradual functionalization of benzo[c][1,2,5]thiadiazole. In total, twenty-one bi(hetero)aryls were prepared in yields ranging from 19 to 95%.
Related Concept Videos
Cycloaddition Reactions: Overview
Photochemical Electrocyclic Reactions: Stereochemistry
Selection Rules: Photochemical Activation
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Aryldiazonium Salts to Azo Dyes: Diazo Coupling
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry

![[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)
