Photoinduced, Direct C(sp(2))-H Bond Azo Coupling of Imidazoheteroarenes and Imidazoanilines with Aryl Diazonium Salts Catalyzed by Eosin Y

Author(s)

Saba, Sumbal ^[1] ; Dos Santos, Caio R. ^[2] ; Zavarise, Bruno R. ^[2] ; Naujorks, Aline A. S. ^[3] ; Franco, Marcelo S. ^[2] ; Schneider, Alex R. ^[2] ; Scheide, Marcos R. ^[2] ; Affeldt, Ricardo F. ^[2] ; Rafique, Jamal ^[3] ; Braga, Antonio L. ^[2]

Affiliation

^[1] Univ Fed ABC, Ctr Ciencias Nat & Humanas CCNH, BR-09210580 Santo Andre, SP - Brazil

^[2] Univ Fed Santa Catarina UFSC, Dept Quim, BR-88040900 Florianopolis, SC - Brazil

^[3] Univ Fed Mato Grosso Sul UFMS, Inst Quim, BR-79074460 Campo Grande, MS - Brazil

• Document type: Journal article
• Source: CHEMISTRY-A EUROPEAN JOURNAL; v. 26, n. 20 FEB 2020.
• Web of Science Citations: 1

Abstract

Herein, a greener approach to the eosin Y-Na-2 catalyzed, C(sp(2))-H bond azo coupling of imidazoheteroarene with aryl diazonium salts is described, under acid free conditions. This direct photoredox process resulted in the corresponding azo products in good to excellent yields. Besides, this new approach could also be applicable to anilines, which is a poorly reactive substrate by other methods. The main features of this reaction are that it provides high yields and is gram-scalable and applicable to biologically relevant imidazoheteroarenes and -anilines. (AU)

• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program