NaIO4-Mediated Selective Oxidation of Alkylarenes and Benzylic Bromides/Alcohols to Carbonyl Derivatives Using Water as Solvent
The Journal of Organic Chemistry2006Vol. 71(13), pp. 5043–5046
Citations Over TimeTop 11% of 2006 papers
Abstract
A new transition-metal-free, sodium metaperiodate (NaIO4)-mediated direct oxidation of methylarenes and benzylic bromides to the corresponding aromatic carboxylic acids is described. Under the same reaction conditions, benzylic alcohols are selectively oxidized to afford the corresponding aldehydes in good yields without undergoing overoxidation. Unprecedentedly, oxidation of benzyl bromide, toluene, or benzyl alcohol with NaIO4 underwent nuclear bromination followed by oxidation to give 4-bromobenzoic acid in 60-79% yields.
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