Reactivity of a 10-I-3 hypervalent iodine trifluoromethylation reagent with phenols

被引：141

作者：

Stanek, Kyrill ^{[1
]}

Koller, Raffael ^{[1
]}

Togni, Antonio ^{[1
]}

机构：

[1] ETH, Dept Chem & Appl Biosci, Swiss Fed Inst Technol, CH-8093 Zurich, Switzerland

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 73卷 / 19期

关键词：

D O I：

10.1021/jo8014825

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of the 10-I-3 hypervalent iodine electrophilic trifluoromethylation reagent 1-trifluoromethyl-1,2-benziodoxol-3-(1H)-one (2) with 2,4,6-trimethylphenol, after deprotonation with NaH and in the presence of 18-crown-6 in a polar, nonprotic solvent, affords 1,3,5-trimethyl-2-(trifluoromethoxy)benzene (4) only as a byproduct. Trifluoromethylation occurs preferentially at the ortho- and para-positions of the aromatic core, giving the corresponding trifluoromethylcyclohexadienones 5 and 6. In case the ortho- and/or para-positions are not Substituted, the corresponding products of all aromatic. electrophilic substitution are obtained in moderate yield, for example, 2-trifluoromethyl-4-tert-butylphenol (10a) from 4-tert-butylphenol (10).

引用

页码：7678 / 7685

页数：8

共 50 条

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