Access to "Friedel Crafts-Restricted" tert-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols
Access to "Friedel Crafts-Restricted" tert-Alkyl Aromatics by Activation/Methylation of Tertiary Benzylic Alcohols
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DOI：
10.1021/jo202371c
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发表时间：
2012-04-06
影响因子：
3.6
通讯作者：
Carlier, Paul R.
中科院分区：
文献类型：
--
作者：
Hartsel, Joshua A.;Craft, Derek T.;Carlier, Paul R.
本文描述了一种制备间叔烷基苯的两步法。用SOCl 2或浓HCl活化合适的叔苄醇，然后用三甲基铝处理，得到68-97%产率的所需产物（22个实施例）。该反应顺序在各种官能团存在下是成功的，包括酸敏感性和路易斯碱性基团。除了t-Bu基团之外，还可以使用该方法安装1，1-二甲基丙基和1-乙基-1-甲基丙基。
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.