Novel Non‐toxic and Non‐hazardous Solvent Systems for the Chemistry of Indoles: Use of a Sulfone‐containing Brønsted Acid Ionic Liquid Catalyst in Butyl Acetate

Abstract : Dipolar and aprotic solvents are often required in acid‐catalyzed reactions, however, many of them are listed in solvent selection guides as not‐recommended due to their toxicity or explosivity. A catalytically functionalized ionic liquid, namely a sulfone‐containing imidazolium‐based Brønsted acid ionic liquid, was synthesized. It alleviates the detrimental effect of classical dipolar aprotic solvents because this ionic liquid integrates the function of a dipolar aprotic solvent able to stabilize carbocation intermediates and the activating effect of a strong Brønsted acid on electrophiles. The use of this tailor‐made ionic liquid was exemplified in some transformation reactions of indoles, which proceeded with high yield and selectivity using a green and an industrially acceptable solvent, butyl acetate. The recyclability of the ionic liquid catalyst was also demonstrated.
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Journal articles
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Submitted on : Wednesday, July 24, 2019 - 12:01:19 PM
Last modification on : Tuesday, September 10, 2019 - 2:10:09 PM

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Ahmed El‐harairy, Y. Qi, Meie Yue, Weigang Fan, Florence Popowycz, et al.. Novel Non‐toxic and Non‐hazardous Solvent Systems for the Chemistry of Indoles: Use of a Sulfone‐containing Brønsted Acid Ionic Liquid Catalyst in Butyl Acetate. ChemCatChem, Wiley, 2019, ⟨10.1002/cctc.201900784⟩. ⟨hal-02193181⟩

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