Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 1, Pages 132-140Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201201100
Keywords
Synthetic methods; Heterogeneous catalysis; Cerium; Regioselectivity; Nitrogen heterocycles; Sulfur; Lewis acids
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Funding
- Ministero dell'Universita e della Ricerca (MIUR) (PRIN 2009)
- Pfizer Ascoli Piceno Plant
- CARIPLO Milano
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Electron-rich aza-aromatic compounds such as indoles and pyrroles are structures of particular interest and importance in organic chemistry. A useful methodology for the regioselective introduction of the sulfenyl group into electron-rich aza-aromatics using S-alkyl-and S-arylthiophthalimides as sulfenylating agents is described. Catalytic amounts of CeCl(3 center dot)7H(2)O/NaI are crucial to the promotion of this regioselective carbon-sulfur-bond-forming electrophilic aromatic substitution reaction. The reaction occurred under mild conditions, and the products were obtained in good to excellent yields. The method represents an efficient preparation of sulfenyl aza-aromatics, which are useful intermediates for important organic transformations, due to the great importance of functionalized indoles among natural compounds and pharmaceutical products.
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