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

页码：2476 / 2481

页数：6

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