Access to "Friedel-Crafts-restricted" tert-alkyl aromatics by activation/methylation of tertiary benzylic alcohols

通过活化/甲基化叔苄醇合成“傅克反应限制的”叔烷基芳烃

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Abstract

Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl(2) or concentrated HCl and then treated with trimethylaluminum, affording the desired products in 68-97% yields (22 examples). This reaction sequence is successful in the presence of a variety of functional groups, including acid-sensitive and Lewis-basic groups. In addition to t-Bu groups, 1,1-dimethylpropyl and 1-ethyl-1-methylpropyl groups can also be installed using this method.

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