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Please login or sign up for a free trial to access the full content. Method 1: Friedel–Crafts Alkylation of Arenes

DOI: 10.1055/sos-SD-045-00097

Zysman-Colman, E.Science of Synthesis, (201045159.

One of the most general methods for synthesizing alkylarenes is via a FriedelCrafts al­kylation reaction,[‌12‌,‌13‌] involving the reversible acid-catalyzed electrophilic aromatic substitution of an alkyl halide or reactive equivalent by an arene.[‌14‌] Mechanistic considerations in electrophilic aromatic substitution reactions, including FriedelCrafts alkylations, have been discussed.[‌15‌,‌16‌] As the product is inevitably more nucleophilic than the starting material, overalkylation is frequently an issue. A primary disadvantage of this reaction is the potential for rearrangement of the carbenium ion intermediate, resulting in a mixture of alkylated products. Product distribution is governed by the severity of the reaction conditions: temperature, nature of the catalyst, and reaction time all influence the reaction outcome.