HFIP-promoted para-selective alkylation of anilines and phenols with tertiary alkyl bromides

被引：8
|
作者：
Huang, Pengcheng [1 ]
Jiang, Xipeng [1 ]
Gao, Du [1 ]
Wang, Cheng [1 ]
Shi, Da-Qing [1 ]
Zhao, Yingsheng [1 ,2 ]
机构：
[1] Soochow Univ, Coll Chem, Key Lab Organ Synth Jiangsu Prov, Chem Engn & Mat Sci, Suzhou 215123, Peoples R China
[2] Henan Normal Univ, Sch Chem & Chem Engn, Xinxiang 453000, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2023年 / 10卷 / 10期
基金：
中国国家自然科学基金;
关键词：
FRIEDEL-CRAFTS ALKYLATIONS; HYDROGEN-FLUORIDE; HYDROARYLATION; ACTIVATION; ALCOHOLS; CHLORIDE; ALKYLBENZENES; CATALYST; ALKENES;
D O I：
10.1039/d3qo00342f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A hexafluoroisopropanol-promoted highly regioselective Friedel-Crafts alkylation of arenes has been developed in this study. Various arenes, including anilides, anisoles, and phenols, were compatible with the reaction, leading to para-alkylated products in moderate to excellent yields. Preliminary mechanistic studies revealed that HFIP acted as a weak Lewis acid to activate haloalkanes and coordinated with arenes through hydrogen bonding to increase the steric hindrance of the coordinated functional group, affording a highly para-selective alkylated product.
引用
收藏
页码：2476 / 2481
页数：6
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