Reactions

Friedel-Crafts alkylation

Abstract

Friedel-Crafts alkylation is an electrophilic aromatic substitution reaction catalyzed by a Lewis acid, in which an alkyl chloride reacts with an aromatic compound to form an alkyl-substituted aromatic.

General reaction scheme of Friedel-Crafts alkylation

Keywords

Aromatic, Alkyl halide, Alkylation, Lewis acid


Category

Aromatic

Mechanism

First, the Lewis Acid coordinates to the halogen atom from the alkyl chloride, increasing the electrophilicity of the carbon and making the halide a better leaving group. This interaction facilitates the departure of the chloride ion, leading to the formation of a carbocation. This electrophile undergoes a nucleophilic attack from the aromatic compound, forming a resonance arenium ion intermediate. Finally, the last step of deprotonation regenerates the aromaticity and the catalyst. An important feature is that the reaction does not occur when the aromatic reagent contains electron-withdrawing group. Indeed, these latter would decrease the electron density of the aromatic, which disfavours the nucleophilic attack.


Chemical mechanism of: Friedel-Crafts alkylation


Recent review

Rueping, M.; Nachtsheim, B. J. A review of new developments in the Friedel–Crafts alkylation–From green chemistry to asymmetric catalysis. Beilstein J. Org. Chem. 2010, 6, 6.