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  • Title: Vanadium-catalyzed sulfenylation of indoles and 2-naphthols with thiols under molecular oxygen.
    Author: Maeda Y, Koyabu M, Nishimura T, Uemura S.
    Journal: J Org Chem; 2004 Oct 29; 69(22):7688-93. PubMed ID: 15497997.
    Abstract:
    Vanadium oxyacetylacetonate [VO(acac)(2)] works as a catalyst for the direct synthesis of 3-sulfanylindoles from indoles and thiols under an atmospheric pressure of molecular oxygen as a reoxidant. For example, the reaction of 2-phenylindole with benzenethiol in the presence of a catalytic amount of VO(acac)(2), potassium iodide, and 2,6-di-tert-butyl-p-cresol in chlorobenzene under molecular oxygen proceeds to afford 2-phenyl-3-(phenylsulfanyl)indole in 86% yield. This catalytic system can also be applied to 2-naphthols instead of indoles to give the corresponding 1-sulfanyl-2-naphthols in up to 57% yield.
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