"Haliranium Ion"-Induced Intermolecular Friedel-Crafts Alkylation in HFIP: Synthesis of β,β-Diaryl α-Halo carbonyl Compounds

被引：5

作者：

Bhattacharya, Aditya ^{[1
]}

Mani Shukla, Pushpendra ^{[1
]}

Maji, Biswajit ^{[1
]}

机构：

[1] Indira Gandhi Natl Tribal Univ, Dept Chem, Anuppur 484886, India

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2021年 / 2021卷 / 33期

关键词：

Arene; beta; beta-Diaryl alpha-halo carbonyl compound; Diastereoselectivity; Friedel-Crafts alkylation; Haliranium ion; SITU GENERATED PALLADIUM; METAL-FREE SYNTHESIS; CYCLOADDITION REACTIONS; FLUORINATED ALCOHOLS; FACILE SYNTHESIS; ACTIVATION; INDOLES; ALKENES; ACCESS; BROMOCYCLIZATION;

D O I：

10.1002/ejoc.202100823

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Here reports a highly regio- and diastereoselective haliranium ion-induced intermolecular Friedel-Crafts reaction of alpha,beta-unsaturated carbonyl compounds in HFIP. The operationally simple and mild method affords the synthetically useful beta,beta-diarylated alpha-halo carbonyl compounds in good yields after a very short reaction time. As an application, a few examples of beta,beta-diarylated olefins are prepared in excellent yields. Based on the experimental results and a qualitative study of 1D-NMR-experiments, a plausible reaction mechanism is proposed.

引用

页码：4737 / 4749

页数：13

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