期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2018, 期 4, 页码 485-493出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201701399
关键词
Electrophilic substitution; Iodine; Hypervalent compounds; Phenols; Synthetic methods
资金
- CONACyT [CB-2013/220836]
- FOMIX [CONACyT-CONCyTEG GTO-2012-C03-194610]
- University of Guanajuato [962/2016]
A new and in situ formed reagent generated by mixing PIFA {bis[(trifluoroacetoxy)iodobenzene]} and AlCl3 was introduced in the organic synthesis for the direct and highly regioselective ortho-chlorination of phenols and phenol ethers. An efficient electrophilic chlorination for these electron-rich arenes as well as the scope of the reaction are described herein. An easy, practical, and open-flask reaction allowed us to introduce a chlorine atom, which is a highly important functional group in organic synthesis. The reproducibility of our method has been demonstrated on gram-scale by carrying out the reaction in 6-bromo-2-naphthol. This halogenation reaction also proceeds in excellent conditions by first preparing the iodine(III)-based chlorinating reagent. Our new chlorinating reagent can be stored at least for two weeks at 4 degrees C without losing its reactivity.
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