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Issue 12, 2016
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Iodosobenzene-mediated direct and efficient oxidation of β-dicarbonyls to vicinal tricarbonyls catalyzed by iron(iii) salts

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Abstract

Iodosobenzene was found to be effective in the direct oxidation of β-dicarbonyls to vicinal tricarbonyl compounds catalyzed by Fe(NO3)·9H2O under mild and environmentally friendly conditions. Also, the present protocol was applied to the one-pot synthesis of heterocyclic compounds via vicinal tricarbonyls as the reactive intermediates. As for the reaction pathway, a plausible mechanism involving iodonium ylide, reactive carbene species and an α-hydroxylated intermediate was proposed.

Graphical abstract: Iodosobenzene-mediated direct and efficient oxidation of β-dicarbonyls to vicinal tricarbonyls catalyzed by iron(iii) salts

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Supplementary files

Article information


Submitted
28 Jul 2016
Accepted
26 Sep 2016
First published
27 Sep 2016

Org. Chem. Front., 2016,3, 1686-1690
Article type
Research Article

Iodosobenzene-mediated direct and efficient oxidation of β-dicarbonyls to vicinal tricarbonyls catalyzed by iron(III) salts

J. Cui, Y. Duan, J. Yu and C. Zhang, Org. Chem. Front., 2016, 3, 1686 DOI: 10.1039/C6QO00405A

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