CCl3CN: A crucial promoter of M CPBA-mediated direct ether oxidation

Article abstract of DOI:10.1021/ol1018079

The direct oxidation of ether sp³ C-H bonds using the new reagent system mCPBA/CCl₃CN/MeCN has been developed. CCl ₃CN in MeCN drastically alters the reactivity of m-chloroperbenzoic acid (mCPBA), and chemoselective transformation of methyl ethers to ketones was realized under mild conditions. Radical-based mCPBA-mediated oxidation was suggested as the reaction mechanism. The present new reaction expands the utility of methyl ethers as stable synthetic precursors of carbonyl compounds and of mCPBA as a radical-based C-H oxidizing agent.