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2014•European Journal of Organic ChemistryRequires access

A Base‐Mediated Mild Sulfenylation of Indoles and Pyrrole with α‐Acylthiones

Caterina Viglianisi, Enrico Marcantoni, Vanessa Carapacchi, Stefano Menichetti, Laura Marsili

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Abstract

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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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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Available abstract

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.

Key concepts: Chemistry, Triethylamine, Pyrrole, Pyridine, Electrophile, Lewis acids and bases, Base (topology), Electrophilic substitution

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