A new procedure for the sulfenylation of indoles and pyrroles based on an aromatic substitution with α-acylthiones used as electrophiles is described. The sulfenylating species were obtained, under very mild reaction conditions, from N-thiophthalimides, using a weak base (pyridine or triethylamine) as promoter. The overall yields obtained are comparable with those obtained by other known sulfenylation protocols, which typically require harsher reaction conditions and/or metal-containing Lewis acids as promoters.
Base-Mediated Mild Sulfenylation of Indoles and Pyrrole with α-Acylthiones / C. Viglianisi; E. Marcantoni; V. Carapacchi; S. Menichetti; L. Marsili. - In: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - ISSN 1099-0690. - STAMPA. - (2014), pp. 6405-6410. [10.1002/ejoc.201402894]
Base-Mediated Mild Sulfenylation of Indoles and Pyrrole with α-Acylthiones
VIGLIANISI, CATERINA;MENICHETTI, STEFANO;
2014
Abstract
A new procedure for the sulfenylation of indoles and pyrroles based on an aromatic substitution with α-acylthiones used as electrophiles is described. The sulfenylating species were obtained, under very mild reaction conditions, from N-thiophthalimides, using a weak base (pyridine or triethylamine) as promoter. The overall yields obtained are comparable with those obtained by other known sulfenylation protocols, which typically require harsher reaction conditions and/or metal-containing Lewis acids as promoters.
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