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45.4.2.1.1.2 Variation 2: Brønsted Acid or Base Catalyzed Friedel–Crafts Alkylation of Arenes with Alkyl Halides

DOI: 10.1055/sos-SD-045-00097

Zysman-Colman, E.Science of Synthesis, (201045161.

FriedelCrafts alkylations with alkyl halides can occur in aqueous or alcoholic solvents in the presence of a Brønsted acid. Under these conditions, hydrolysis of the alkyl halide occurs with concomitant generation of small equilibrium concentrations of reactive carbenium ions. The use of Brønsted acids generally affords similar regioisomeric distribution products as with Lewis acids. Increasing the Brønsted acidity of the catalyst does affect the chemoselectivity in reactions where there is competition amongst arene nucleophiles, the more nucleophilic arene being the preferred substrate.[‌21‌]

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