Direct Bis-Alkyl Thiolation for Indoles with Sulfinothioates under Pummerer-Type Conditions.

A base-free bis-alkyl thiolation reaction of indoles with sulfinothioates under Pummerer-type conditions is described. Sulfinothioates, activated with 2,2,2-trifluoroacetic anhydride, are demonstrated to be an efficient thiolation reagent for wide applications. This approach enabled double C-H thiolation at the C2 and C3 of the indole in one pot. The mechanism studies suggested the thiolation was realized through the sulfoxonium salt rather than sulfenyl carboxylate.

Citation

Peng Qi, Fang Sun, Ning Chen, Hongguang Du. Direct Bis-Alkyl Thiolation for Indoles with Sulfinothioates under Pummerer-Type Conditions. The Journal of organic chemistry. 2022 Jan 21;87(2):1133-1143

Mesh Tags

Substances

PMID: 35014848

search → result