NaIO4-mediated selective oxidation of alkylarenes and benzylic bromides/alcohols to carbonyl derivatives using water as solvent.
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.
Shaikh
Tanveer Mahammad Ali
TM
Chemical Engineering & Process Development Division, National Chemical Laboratory, Pashan Road, Pune, India 411008.
Emmanuvel
Lourdusamy
L
Sudalai
Arumugam
A
D000438:Alcohols / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D001965:Bromides / Q000737:chemistry*; D007659:Ketones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010504:Periodic Acid / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000438:Alcohols; D001555:Benzene Derivatives; D001593:Benzyl Compounds; D001965:Bromides; D007659:Ketones; D012997:Solvents; D014867:Water; D010504:Periodic Acid; C009288:metaperiodate