Polyoxometalate-based ionic liquids: efficient reversible phase transformation-type catalysts for thiolation of alcohols to construct C-S bonds.
Dalton Trans
; 53(10): 4492-4500, 2024 Mar 05.
Article
en En
| MEDLINE
| ID: mdl-38348738
ABSTRACT
As important building blocks in natural products and organic synthesis, thioethers have a wide range of potential applications. Herein, polyoxometalate-based ionic liquids (POM-ILs-SO3H) derived from N-alkyl imidazole were synthesized and used for the first time for the thiolation of alcohols to construct C-S bonds in a series of benzyl thioethers. This type of POM-ILs-SO3H catalyst exhibited high catalytic activity, providing up to 98% yield of thioether within 1 h at 70 °C. The alkyl chain length of the imidazole had a certain effect on the solubility of the POM-ILs-SO3H catalysts in the reaction solvent, and then affected their catalytic activity. The catalytic system had a wide substrate scope and was suitable for the reaction of tertiary and secondary benzyl alcohols with thiophenols or cycloalkyl thiols. In particular, [PIMPS]3PW12O40 (PIM = 1-propylimidazole, PS = propane sulfonate) as a reversible phase transformation-type catalyst, combining the advantages of homogeneous and heterogeneous catalysts, exhibited high activity and good recyclability with only a slight decrease in the yield after five runs. Additionally, a carbocation mechanism was proposed for the thiolation reaction of alcohols.
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01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
Dalton Trans
Asunto de la revista:
QUIMICA
Año:
2024
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Article