Synthesis of ferrocenyl- and hetaryl-substituted 2,2,2-trifluoroethanols and their conversion into 2,2,2-trifluoroethanethiols using Lawesson’s reagent

• A series of hetaryl and ferrocenyl substituted ketones was synthesized.
• Nucleophilic trifluoromethylation of hetaryl and ferrocenyl ketones was performed.
• Hetaryl/ferrocenyl substituted 2,2,2-trifluoroethanols were obtained in high yields.
• Selected 2,2,2-trifluoroethanols were treated with LR or Py/P2S5 complex in toluene.
• New hetaryl/ferrocenyl substituted 2,2,2-trifluoroethanethiols were obtained.

Ferrocenyl- and hetaryl-substituted ketones react smoothly with the Ruppert-Prakash reagent and, after desilylation of the intermediate adduct, gave the corresponding tertiary 2,2,2-trifluoroethanols. Similarly, ferrocenyl carbaldehyde was converted into 1-ferrocenyl-2,2,2-trifluoroethanol via nucleophilic trifluoromethylation. Some of the obtained fluorinated alcohols were transformed into thiols by treatment with Lawesson’s reagent or P2S5·2C5H5N complex. Remarkably, the obtained thiols are non-odorous compounds.

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