Elsevier

Tetrahedron Letters

Volume 34, Issue 39, 24 September 1993, Pages 6245-6246
Tetrahedron Letters

Thiomethylation of indole and haloindole zinc salts

https://doi.org/10.1016/S0040-4039(00)73721-XGet rights and content

Abstract

Thiomethylation of indole and haloindoles has been achieved via their zinc salts. This one-pot reaction uses methyl disulfide as electrophile. Isolation of thiomethylated indole products in moderate yields requires the addition of a thiol (e.g., cysteine hydrochloride) during aqueous workup, facilitating the displacement of the thiomethylated product from a water-insoluble zinc salt.

A one-pot synthesis of 3-(thiomethyl)indoles 2 from the zinc salts of indole and haloindoles 1 is described.

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References (3)

  • K. Tomita et al.

    Heterocycles

    (1976)
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