Catalyzed and Promoted Aliphatic Fluorination

被引:41
作者
Bume, Desta Doro [1 ]
Harry, Stefan Andrew [1 ]
Lectka, Thomas [1 ]
Pitts, Cody Ross [2 ]
机构
[1] Johns Hopkins Univ, Dept Chem, 3400 North Charles St, Baltimore, MD 21218 USA
[2] Swiss Fed Inst Technol, Dept Chem & Appl Biosci, Vladimir Prelog Weg 2, CH-8093 Zurich, Switzerland
基金
美国国家科学基金会;
关键词
C-H FLUORINATION; ORGANOCATALYTIC ALPHA-CHLORINATION; ELECTRON-TRANSFER; FLUORONIUM ION; AMINO-ACIDS; SPECTROSCOPIC CHARACTERIZATION; ENANTIOSELECTIVE FLUORINATION; DECARBOXYLATIVE FLUORINATION; STEREOSELECTIVE-SYNTHESIS; BENZYLIC FLUORINATION;
D O I
10.1021/acs.joc.8b00982
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
In the last six years, the direct functionalization of aliphatic C-H (and C-C) bonds through user-friendly, radical-based fluorination reactions has emerged as an exciting research area in fluorine chemistry. Considering the historical narratives about the challenges of developing practical radical fluorination in organic frameworks, notable advancements in controlling both reactivity and selectivity have been achieved during this time. As one of the participants in the field, herein, we a provide brief account of research efforts in our laboratory from the initial discovery of radical monofluorination on unactivated C-H bonds in 2012 to more useful strategies to install fluorine on biologically relevant molecules through directed fluorination methods. In addition, accompanying mechanistic studies that have helped guide reaction design are highlighted in context.
引用
收藏
页码:8803 / 8814
页数:12
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