Introduction of a hydroxy group at the para position and N-iodophenylation of N-arylamides using phenyliodine(III) bis(trifluoroacetate)

被引:86
作者
Itoh, N [1 ]
Sakamoto, T [1 ]
Miyazawa, E [1 ]
Kikugawa, Y [1 ]
机构
[1] Josai Univ, Fac Pharmaceut Sci, Sakado, Saitama 3500295, Japan
关键词
D O I
10.1021/jo0260847
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of anilides with phenyliodine(III) bis(trifluoroacetate) (PIFA) in trifluoroacetic acid (TFA), TFA-CHCl3, or hexafluoroisopropyl alcohol (HFIP) is described. When the acyl group of the anilide is highly electronegative, such as trifluoroacetyl, or the phenyl group is substituted with an electron-withdrawing group, the 4-iodophenyl group is transferred from PIFA to the amide nitrogen to afford acetyldiarylamines. On the other hand, when the acyl group contains an electron-donating function, such as 4-methoxyphenyl, or the phenyl group is substituted with an electron-donating group, a trifluoroacetoxy group is transferred to the para position of the anilide aromatic ring. This group is hydrolyzed during workup to produce the corresponding phenol.
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页码:7424 / 7428
页数:5
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