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Protic ionic liquids as recyclable solvents for the acid catalysed synthesis of diphenylmethyl thioethers
journal contributionposted on 2013-07-01, 00:00 authored by Luke HendersonLuke Henderson, Megan Thornton, Nolene ByrneNolene Byrne, Bronwyn Fox, Kelsey Waugh, Jennifer Suzanne Squire, Linden Servinis, Joshua Delaney, H L Brozinski, L M Andrighetto, Jarrad Altimari
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.