The facile and efficient oxidation of various alcohols such as benzylic alcohols, primary alcohols, secondary alcohols, and diols in water using the hypervalent iodine(III) reagent, iodosobenzene (PhI=O), with KBr is described. Electrospray ionization (ESI) mass spectrometric studies on the behavior of PhI=O-KBr in aqueous solution suggested that these reactions are induced by the formation of highly reactive iodine species [PhI(Br)nO –]. Further development to recyclable polymer-supported iodine(III) reagent extends the utility of this reaction to afford an environmentally benign method.
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Tohma et al. (2002) studied this question.