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.
- 6-bromo-, 6-chloro-, 5-bromo-, and 5-fluoro-3-(thiomethyl)indole
- indole, thiomethylation of
ASJC Scopus subject areas
- Organic Chemistry
- Drug Discovery