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

K Stanek, R Koller, A Togni

Index: Stanek, Kyrill; Koller, Raffael; Togni, Antonio Journal of Organic Chemistry, 2008 , vol. 73, # 19 p. 7678 - 7685

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Citation Number: 95

Abstract

The reaction of the 10-I-3 hypervalent iodine electrophilic trifluoromethylation reagent 1- trifluoromethyl-1, 2-benziodoxol-3-(1 H)-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 ...