Access to %26quot;Friedel Crafts-Restricted%26quot; tert-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols

作者:Hartsel Joshua A; Craft Derek T; Chen Qiao Hong; Ma Ming; Carlier Paul R*
来源:Journal of Organic Chemistry, 2012, 77(7): 3127-3133.
DOI:10.1021/jo202371c

摘要

Herein we describe a two-step protocol to prepare m-tert-alkylbenzenes. The appropriate tertiary benzylic alcohols are activated with SOCl2 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.

  • 出版日期2012-4-6
  • 单位Virginia Tech; 美国弗吉尼亚理工大学(Virginia Tech)