Catalytic Friedel-Crafts Reactions of Highly Electronically Deactivated Benzylic Alcohols

被引：178
作者：
Vukovic, Vuk D. [1 ]
Richmond, Edward [1 ]
Wolf, Elena [1 ]
Moran, Joseph [1 ]
机构：
[1] Univ Strasbourg, CNRS, ISIS UMR 7006, F-67000 Strasbourg, France
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 11期
基金：
欧洲研究理事会;
关键词：
alcohols; Bronsted acid catalysis; carbenium ion; Friedel-Crafts; hexafluoro-2-propanol; PI-ACTIVATED ALCOHOLS; FLUORINATED ALCOHOLS; PROPARGYLIC ALCOHOLS; AROMATIC-COMPOUNDS; CATION REACTIVITY; ALKYLATION; HEXAFLUOROISOPROPANOL; CARBOCATIONS; SUBSTITUTION; SULFONATES;
D O I：
10.1002/anie.201612573
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Highly electronically deactivated benzylic alcohols, including those with a CF3 group adjacent to the OH-bearing carbon, undergo dehydrative Friedel-Crafts reactions upon exposure to catalytic Bronsted acid in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) solvent. Titration and kinetic experiments support the involvement of higher order solvent/acid clusters in catalysis.
引用
收藏
页码：3085 / 3089
页数：5
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