Gallium(III) trifluormethanesulfonate: A water-tolerant, reusable Lewis acid catalyst for Friedel-Crafts reactions

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The application of gallium(III) trifluoromethanesulfonate (triflate, OTf) in Friedel-Crafts alkylation and acylation reactions is described. Gallium triflate was found to be an excellent catalyst for the adamantylation of toluene with 1-bromoadamantane, where its activity was compared to that of well-known rare earth metal triflates. As Ga(OTf)3 does not decompose in the presence of water the isopropylation of aromatics can be carried out with isopropyl alcohol in moderate to excellent yields. While acetylation provides moderate yields in selective reactions, benzoylation of aromatics takes place in good yields in a catalytic and non-stoichiometric reaction. The catalyst can easily be recovered from the reaction mixture and can be reused without loss of activity, demonstrating its effective and environmentally friendly recyclable character.

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Catalysis Letters