Solvent-free Brønsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols

A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct SN1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Brønsted acid o-benzenedisulfonimide under neat conditions is herein reported. A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and high regioselectivity. The observed reactivity was shown to be in agreement with Mayr's nucleophilicity and electrophilicity scales.

Graphical abstractDownload high-res image (232KB)Download full-size imageA library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and regioselectivity via a simple and efficient alkylation of aromatic compounds through direct SN1-type alcohol nucleophilic substitution in the presence of o-benzenedisulfonimide under neat conditions.