A cooperative allylic fluorination: combination of nucleophilic and electrophilic fluorine sources

被引：27

作者：

Bloom, Steven ^{[1
]}

Knippel, James Levi ^{[1
]}

Holl, Maxwell Gargiulo ^{[1
]}

Barber, Ross ^{[1
]}

Lectka, Thomas ^{[1
]}

机构：

[1] Johns Hopkins Univ, Dept Chem, Baltimore, MD 21218 USA

来源：

TETRAHEDRON LETTERS | 2014年 / 55卷 / 33期

关键词：

Fluorine; Allylic; Methodology; Alkene; C-H FLUORINATION; DECARBOXYLATIVE FLUORINATION; SELENIUM DIOXIDE; OXIDATION; SELECTFLUOR;

D O I：

10.1016/j.tetlet.2014.05.093

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one step, regioselective allylic fluorination of alkenes is reported in which electrophilic and nucleophilic sources of fluorine act synergistically to afford rearranged allylic fluorides over alternative vicinal dihalides. The reaction occurs under exceptionally mild conditions and without need for prefunctionalization or transition metal catalysts. The fluorination of cyclic alkenes and monoterpenes is highlighted, and preliminary mechanistic experiments reveal that dual (radical and ionic) pathways operate simultaneously. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：4576 / 4580

页数：5

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