Aluminum Trifluoromethanesulfonate

Introduction

The synthesis of aluminum trifluoromethanesulfonate from aluminum trichloride and triflic acid was published by Olah et al.[1] [2] in 1988. Aluminum triflate is a white solid with a high melting point[2] and acts as a strong, stable, oxophilic[3–5] Lewis acid that can easily be recycled and reused[6] due to its water-tolerant properties.[7] During initial investigations, aluminum trifluoromethanesulfonate was mainly used for Michael and Friedel–Crafts reactions, and it also functioned as a Lewis acid catalyst for the protection of alcohols, phenols, and thiophenols[8] with a variety of different protecting groups (i.e., methyl, ethyl, isopropyl, tert-butyl, acetyl, tetrahydropyranyl and tetrahydrofuranyl).[1] [9] [10] Recently, the utilization of aluminum trifluoromethanesulfonate has been studied in much more diversity, for example as a co-catalyst in metal-catalyzed reactions,[4] [11] in the nucleophilic opening of epoxides,[5] [12] [13] cyclization,[14] substitution,[15] and other reactions.

• References

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• 2 Olah GA. US Patent 5,110,778, 1992
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• 17 Gohain M, Jacobs J, Marais C, Bezuidenhoudt BC. B. Aust. J. Chem. 2013; in press
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• 19 Serdyn M.; M.Sc. Thesis; University of the Free State, Bloemfontein, 2013.