Indium(I) iodide promoted cleavage of dialkyl disulfides--application of the Michael addition of thiolate anions to conjugated carbonyl compounds and regioselective ring opening of epoxides.

Canadian Journal of Chemistry | May 1, 2006| | Copyright

Abstract: Indium(I) iodide promotes cleavage of dialkyl disulfides generating thiolate anions that then undergo facile addition to [alpha],[beta]-unsaturated ketones, aldehydes, carboxylic esters, and nitriles under neutral conditions producing corresponding [beta]-ketosulfides or [beta]-cyanosulfides. This strategy has also been used for the regioselective nucleophilic ring opening of epoxides by thiolate anions in presence of indium(III) chloride producing corresponding [beta]-hydroxyphenyl sulfides. The reactions are in general, very clean, high yielding, and reasonably ...

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