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

Autor(es)

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

Afiliação do(s) autor(es)

^[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

• Tipo de documento: Artigo Científico
• Fonte: Tetrahedron; v. 74, n. 29, p. 3971-3980, JUL 19 2018.
• Citações Web of Science: 9

Resumo

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)

• Processo FAPESP: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Beneficiário: Arlene Gonçalves Corrêa
• Modalidade de apoio: Auxílio à Pesquisa - Programa Centros de Pesquisa em Engenharia