Iodine-catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant under ambient conditions in dimethyl carbonate

The iodine catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant has been achieved under ambient conditions, providing a convenient and efficient method for the synthesis of 3-sulfenylindoles in good to excellent yields and with high selectivity. The reactio...

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Bibliographic Details
Published in:Green chemistry : an international journal and green chemistry resource : GC 2012-01, Vol.14 (7), p.2066-2070
Main Authors: Ge, Wenlei, Wei, Yunyang
Format: Article
Language:English
Subjects:
Catalysis
Chemistry
Exact sciences and technology
General and physical chemistry
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
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Summary:The iodine catalyzed oxidative system for 3-sulfenylation of indoles with disulfides using DMSO as oxidant has been achieved under ambient conditions, providing a convenient and efficient method for the synthesis of 3-sulfenylindoles in good to excellent yields and with high selectivity. The reaction was carried out in a green solvent, DMC, under atmospheric conditions. Only 0.5 mmol of disulfide was needed for the 3-sulfenylation of 1 mmol of indole because both the sulfenyl groups of a symmetric disulfide take part in the reaction. The procedure is suitable for N-protected or unprotected indoles.
ISSN:1463-9262
1463-9270
DOI:10.1039/c2gc35337g