SITE-SELECTIVE FLUORINATION OF ORGANIC-COMPOUNDS USING 1-ALKYL-4-FLUORO-1,4-DIAZABICYCLO[2.2.2]OCTANE SALTS (SELECTFLUOR REAGENTS)

被引:246
作者
LAL, GS
机构
[1] Corporate Science and Technology Center, Air Products and Chemicals, Inc., Allentown
关键词
D O I
10.1021/jo00062a023
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The new ''N-F''-type electrophilic reagent family of 1-alkyl-4-fluoro-1,4-diazabicyclo[2.2.2]octane salts8d (derived from elemental fluorine (F2) and 1-alkyl-1,4-diazabicyclo[2.2.2]octane salts) has been found to be very effective for the fluorination of a wide variety of organic substrates. These include steroidal enol acetates and silyl enol ethers, phenyl-substituted olefins, sulfides bearing alpha-H atoms, certain carbanions, and mildly activated aromatic compounds. The products were obtained with good yields and regioselectivity under very mild reaction conditions.
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页码:2791 / 2796
页数:6
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