Mild Silver-Mediated Geminal Difluorination of Styrenes Using an Air- and Moisture-Stable Fluoroiodane Reagent

被引：130

作者：

Ilchenko, Nadia O. ^{[1
]}

Tasch, Boris O. A. ^{[1
]}

Szabo, Kalman J. ^{[1
]}

机构：

[1] Stockholm Univ, Dept Organ Chem, Stockholm, Sweden

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2014年 / 53卷 / 47期

基金：

瑞典研究理事会;

关键词：

fluorine; hypervalent compounds; reaction mechanism; rearrangement; silver; HYPERVALENT IODINE REAGENTS; ARYL BORONIC ACIDS; ELECTROPHILIC TRIFLUOROMETHYLATION; LYSOPHOSPHATIDIC ACID; ORGANOBORON COMPOUNDS; FUNCTIONAL-GROUPS; FLUORINATION; DIFLUOROMETHYLATION; IODIDES; ARENES;

D O I：

10.1002/anie.201408812

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

An air-and moisture-stable fluoroiodane in the presence of AgBF4 is suitable for selective geminal difluorination of styrenes under mild reaction conditions. One of the C-F bonds is formed by transfer of electrophilic fluorine from the hypervalent iodine reagent, while the other one arises from the tetrafluoroborate counterion of silver. Deuterium-isotope-labelling experiments and rearrangement of methyl styrene substrates suggest that the reaction proceeds through a phenonium ion intermediate.

引用

页码：12897 / 12901

页数：5

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