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Issue 12, 2018
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A metal-free and mild approach to 1,3,4-oxadiazol-2(3H)-ones via oxidative C–C bond cleavage using molecular oxygen

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Abstract

A mild metal-free approach to 1,3,4-oxadiazol-2(3H)-ones via 1,3,4-oxadiazin-5(6H)-ones is described. This novel transformation, promoted by the electron-withdrawing p-substituents on the phenyl group at the α-carbonyl position, features a tandem reaction consisting of oxidative hydroxylation and C–C bond cleavage using molecular oxygen. The method utilizes K2CO3 in CH3CN without any oxidants, transition metals, or additives, enabling the tunable synthesis of 1,3,4-oxadiazin-5(6H)-ones, 1,3,4-oxadiazol-2(3H)-ones, and α-ketoamides under mild aerobic conditions.

Graphical abstract: A metal-free and mild approach to 1,3,4-oxadiazol-2(3H)-ones via oxidative C–C bond cleavage using molecular oxygen

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Publication details

The article was received on 28 Dec 2017, accepted on 01 Mar 2018 and first published on 02 Mar 2018


Article type: Paper
DOI: 10.1039/C7OB03188B
Citation: Org. Biomol. Chem., 2018,16, 2105-2113
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    A metal-free and mild approach to 1,3,4-oxadiazol-2(3H)-ones via oxidative C–C bond cleavage using molecular oxygen

    B. Lim, S. Park, J. H. Park, J. Gam, S. Kim, J. W. Yang and J. Lee, Org. Biomol. Chem., 2018, 16, 2105
    DOI: 10.1039/C7OB03188B

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