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A Base‐Mediated Mild Sulfenylation of Indoles and Pyrrole with α‐Acylthiones
Author(s) -
Viglianisi Caterina,
Marcantoni Enrico,
Carapacchi Vanessa,
Menichetti Stefano,
Marsili Laura
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402894
Subject(s) - chemistry , triethylamine , pyrrole , pyridine , electrophile , lewis acids and bases , base (topology) , electrophilic substitution , electrophilic aromatic substitution , combinatorial chemistry , organic chemistry , reaction conditions , medicinal chemistry , catalysis , mathematical analysis , mathematics
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.