Protic ionic liquids as recyclable solvents for the acid catalysed synthesis of diphenylmethyl thioethers |
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| Authors: | Luke C. Henderson Megan T. Thornton Nolene Byrne Bronwyn L. Fox Kelsey D. Waugh Jennifer S. Squire Linden Servinis Joshua P. Delaney Hannah L. Brozinski Luke M. Andrighetto Jarrad M. Altimari |
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| Affiliation: | 1. Institute for Frontier Materials, Deakin University, Waurn Ponds Campus, Geelong, 3216, Victoria, Australia;2. Strategic Research Center for Chemistry and Biotechnology, Deakin University, Pigdons Road, Waurn Ponds Campus, Geelong, 3216, Victoria, Australia |
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| Abstract: | The acid catalysed formation of diphenylmethyl (DPM) thioethers was successfully achieved using the protic ionic liquid (pIL) triethylamine:methanesulfonic acid (TeaMs) as the reaction solvent under microwave irradiation. A slight excess of methanesulfonic acid (10% v/v) was required to facilitate the reaction, which was applied to a variety of thiols. Aliphatic, aromatic and heterocyclic aromatic thiols were converted to their corresponding DPM thioethers in high yields (63–99%), in short reaction times (5–20 min) and using mild temperatures (80–100 °C). Finally, the pIL (TeaMS) was recycled five times without loss of yield. |
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| Keywords: | Protic ionic liquid Thioether Thiol Microwave irradiation |
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