One of the reactions in my synthesis process is to oxidate a methyl group at benzyl position into an aldehyde group using K2S2O8 as oxidant and CuSO4 as catalyst. I want to know what the mechanism of this reaction is? Thanks.
Eric B. J. Harris
This is a radical mediated reaction with CuSO4 acting as a single electron transport catalyst with K2S2O8 generating anionic sulfate radicals. These abstract hydrogen to generate KHSO4 and a benzyl radical which rapidly combines with Cu(II) to form an organocopper(III) intermediate which reductively eliminates to form Cu(I) which is reoxidised to Cu(II) by the persulfate. The resulting benzyl alcohol is further oxidised to the aldehyde in a similar fashion.
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