CCl3CN: a crucial promoter of mCPBA-mediated direct ether oxidation.
The direct oxidation of ether sp(3) C-H bonds using the new reagent system mCPBA/CCl(3)CN/MeCN has been developed. CCl(3)CN 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.
Kamijo
Shin
S
Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Matsumura
Shoko
S
Inoue
Masayuki
M
D002723:Chlorobenzoates / Q000737:chemistry*; D004987:Ethers / Q000737:chemistry*; D005609:Free Radicals / Q000737:chemistry; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*; D010084:Oxidation-Reduction; D012997:Solvents
C554258:CCl3CN compound; D002723:Chlorobenzoates; D004987:Ethers; D005609:Free Radicals; D006843:Hydrocarbons, Chlorinated; D009570:Nitriles; D012997:Solvents; C000433:3-chloroperbenzoic acid