Oxovanadium complex-catalyzed aerobic oxidation of propargylic alcohols

被引：183

作者：

Maeda, Y

Kakiuchi, N

Matsumura, S

Nishimura, T

Kawamura, T

Uemura, S ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Energy & Hydrocarbon Chem, Sakyo Ku, Kyoto 6068501, Japan

[2] Gifu Univ, Fac Engn, Dept Chem, Gifu 5011193, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2002年 / 67卷 / 19期

关键词：

D O I：

10.1021/jo025918i

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A catalytic system consisting of vanadium oxyacetylacetonate [VO(acac)(2)] and 3 Angstrom molecular sieves (MS3A) in acetonitrile works effectively for the aerobic oxidation of propargylic alcohols [(RCH)-C-1-(OH)Cequivalent toCR(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.

引用

收藏

页码：6718 / 6724

页数：7

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