Alumina, iodobenzene diacetate oxidation

Scheme 6.33 Oxidation of alcohols using alumina-supported iodobenzene diacetate.

Varma et al. reported the use of supported iodobenzene diacetate (IBD) as an oxidant. With alumina as a support, the yields improved markedly compared to those obtained with neat IBD (Scheme 4) [47]. IBD-alumina has also been used for the rapid, high-yielding and selective oxidation of alkyl, aryl and cyclic sulfides to the corresponding sulfoxides upon microwave irradiation [48]. 

Organohypervalent iodine reagents such as iodoxybenzene, o-iodoxybenzoic acid (IBX), bis(trifluoroacetoxy)iodobenzene (BTI), and Dess-Marhn periodinane have been used for the oxidation of alcohols and phenols. Most of these reactions are conducted in high-boiling DMSO or relahvely toxic acetonitrile, which increase the burden on the environment. Further, the use of inexpensive iodobenzene diacetate (IBD) as an oxidant has not been fully exploited. Varma et al. have reported the first use of supported iodobenzene diacetate as an oxidant. In this novel oxidative protocol, alumina-supported IBD under solvent-free conditions rapidly converts alcohols to the corresponding carbonyl compounds in almost quantitative yields. The use of alumina as a support improved the yields markedly as compared to neat IBD (Scheme 2.2-40). 1,2-Benzenedimethanol, however, undergoes cyclization to afford l(3H)-isobenzofuranone [116]... 

Varma et al. (1998) used alumina-supported iodobenzene diacetate (IBD) as an oxidant for the rapid oxidation of alcohols to carbonyl compounds under microwave irradiation. This reaction takes 1-3 min and provides excellent yields. 

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See also in sourсe #XX -- [ ]

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