Thiomethylation of indole and haloindole zinc salts

Cindy C Browder, Miguel O. Mitchell, Rhonda L. Smith, Gibran el-Sulayman

Research output: Contribution to journalArticle

36 Citations (Scopus)

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.

Original languageEnglish (US)
Pages (from-to)6245-6246
Number of pages2
JournalTetrahedron Letters
Volume34
Issue number39
DOIs
StatePublished - Sep 24 1993
Externally publishedYes

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Zinc
Salts
Sulfhydryl Compounds
Cysteine
Water
indole
dimethyl disulfide

Keywords

  • 6-bromo-, 6-chloro-, 5-bromo-, and 5-fluoro-3-(thiomethyl)indole
  • indole, thiomethylation of

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Thiomethylation of indole and haloindole zinc salts. / Browder, Cindy C; Mitchell, Miguel O.; Smith, Rhonda L.; el-Sulayman, Gibran.

In: Tetrahedron Letters, Vol. 34, No. 39, 24.09.1993, p. 6245-6246.

Research output: Contribution to journalArticle

Browder, CC, Mitchell, MO, Smith, RL & el-Sulayman, G 1993, 'Thiomethylation of indole and haloindole zinc salts', Tetrahedron Letters, vol. 34, no. 39, pp. 6245-6246. https://doi.org/10.1016/S0040-4039(00)73721-X
Browder, Cindy C ; Mitchell, Miguel O. ; Smith, Rhonda L. ; el-Sulayman, Gibran. / Thiomethylation of indole and haloindole zinc salts. In: Tetrahedron Letters. 1993 ; Vol. 34, No. 39. pp. 6245-6246.
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