NH4I-catalyzed chalcogen(S/Se)-functionalization of 5-membered N-heteroaryls under metal-free conditions

Author(s)

Bettanin, Luana ^[1] ; Saba, Sumbal ^[1] ; Doerner, V, Carlos ; Franco, Marcelo S. ^[2] ; Godoi, Marcelo ^[3] ; Rafique, Jamal ^[2] ; Braga, Antonio L. ^[2]

Affiliation

^[1] Univ Fed Santa Catarina, Dept Quim, BR-88040970 Florianopolis, SC - Brazil

^[2] Doerner, Carlos, V, Univ Fed Santa Catarina, Dept Quim, BR-88040970 Florianopolis, SC - Brazil

^[3] Univ Fed Rio Grande, Escola Quim & Alimentos, Campus Santo Antonio da Patrulha, Santo Antonio Patrulha, RS - Brazil

• Document type: Journal article
• Source: Tetrahedron; v. 74, n. 29, p. 3971-3980, JUL 19 2018.
• Web of Science Citations: 9

Abstract

Herein, we described the NH4I-catalyzed C-H bond chalcogenation of N-heteroaryls in the presence of a minimum amount of DMSO/H2O/acetic acid as additives (2.5/2.5/1 M equiv., respectively), under metal-free conditions. Under optimized conditions, a wide variety of sulfenyl/selenyl imidazo{[}1,2-alpha]pyridines were prepared in very good yields. Moreover, the present approach was also highly efficient for the chalcogenation of different 5-membered N-heteroaryls, e.g., indole, imidazothiazole, indazole and imidazopyrimidine derivatives. (C) 2018 Elsevier Ltd. All rights reserved. (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