Fe(III)/NaBH4-Mediated Free Radical Hydrofluorination of Unactivated Alkenes

被引：272
作者：
Barker, Timothy J.
Boger, Dale L. [1 ]
机构：
[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2012年 / 134卷 / 33期
基金：
美国国家卫生研究院;
关键词：
ELECTROPHILIC FLUORINATION; ARYL FLUORIDES; OLEFINS; ANALOGS; HYDROAZIDATION; SELECTFLUOR; VINBLASTINE; DERIVATIVES; PALLADIUM; REAGENTS;
D O I：
10.1021/ja3063716
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A powerful Fe(III)/NaBH4-mediated free radical hydrofluorination of unactivated alkenes is disclosed using Selectfluor reagent as a source of fluorine and resulting in exclusive Markovnikov addition. In contrast to the traditional and unmanageable free radical hydrofluorination of alkenes, the Fe(III)/NaBH4-mediated reaction is conducted under exceptionally mild reaction conditions (0 degrees C, 5 min, CH3CN/H2O). The reaction can be conducted open to the air and with water as a cosolvent and demonstrates an outstanding substrate scope and functional group tolerance.
引用
收藏
页码：13588 / 13591
页数：4
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