Benign and efficient preparation of thioethers by solvent-free S-alkylation of thiols with alkyl halides catalyzed by potassium fluoride on alumina

ABSTRACT

The preparation of thioethers by S-alkylation of various thiols with alkyl halides under solvent-free reaction conditions using potassium fluoride on alumina (KF/Al₂O₃) as a solid catalyst has been investigated in detail with respect to three different modes of reaction activation (ultrasound irradiation, microwave irradiation, and conventional heating) for obtaining maximum yield of the thioether. The importance of KF/Al₂O₃ as a particularly efficient catalyst was corroborated for all three modes of reaction activation, although the reaction time was found to be strongly dependent on the mode of activation. The yield of the thioethers was also found to depend on the amount of the solid catalyst relative to the equimolar amounts of the two reactants.

GRAPHICAL ABSTRACT

KEYWORDS:

• Potassium fluoride on alumina
• thioether
• ultrasound irradiation
• microwave irradiation
• solvent-free reaction

Funding

We are grateful to Vietnam National Foundation for Science and Technology Development (NAFOSTED) under grant number [104.01-2011.40] for financial support.