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HERO ID
7903035
Reference Type
Journal Article
Title
NaIO4-mediated selective oxidation of alkylarenes and benzylic bromides/alcohols to carbonyl derivatives using water as solvent
Author(s)
Shaikh, TM; Emmanuvel, L; Sudalai, A
Year
2006
Is Peer Reviewed?
Yes
Journal
Journal of Organic Chemistry
ISSN:
0022-3263
EISSN:
1520-6904
Volume
71
Issue
13
Page Numbers
5043-5046
Language
English
PMID
16776545
DOI
10.1021/jo0606305
Web of Science Id
WOS:000238312300051
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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