Oxovanadium complex-catalyzed aerobic oxidation of propargylic alcohols |
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Authors: | Maeda Yasunari Kakiuchi Nobuyuki Matsumura Satoshi Nishimura Takahiro Kawamura Takashi Uemura Sakae |
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Institution: | Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Sakyo-ku, Kyoto 606-8501, Japan. |
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Abstract: | A catalytic system consisting of vanadium oxyacetylacetonate VO(acac)(2)] and 3 A molecular sieves (MS3A) in acetonitrile works effectively for the aerobic oxidation of propargylic alcohols R(1)CH(OH)Ctbd1;CR(2)] to the corresponding carbonyl compounds under an atmospheric pressure of molecular oxygen. Although the reactivity of alpha-acetylenic alkanols (R(1) = alkyl) is lower compared to that of the alcohols of R(1) = aryl, alkenyl, and alkynyl, the use of VO(hfac)(2) as a catalyst and the addition of hexafluoroacetylacetone improve the product yield in these cases. A catalytic cycle involving a vanadium(V) alcoholate species and beta-hydrogen elimination from it has been proposed for this oxidation. |
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