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A Mild, Catalytic, and Highly Selective Method for the Oxidation of α,β-Enones to 1,4-Enediones

Jin-Quan Yu and E. J. Corey*

*Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, Email:

J.-Q. Yu, E. J. Corey, J. Am. Chem. Soc., 2003, 125, 3232-3233.

DOI: 10.1021/ja0340735


A new and simple method is described for the one-step oxidation of α,β-enones to 1,4-enediones in good yields using t-butylhydroperoxide as stoichiometric oxidant and 20% Pd(OH)2 on carbon as catalyst. The same reagents have been used to convert ethylene ketals of α,β-enones to the corresponding monoethylene ketals of 1,4-enediones. The mechanism is discussed.

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Key Words

tert-butylhydroperoxide, enones

ID: J48-Y2003-1360