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Selective cross-dehydrogenative C–O coupling of N-hydroxy compounds with pyrazolones. Introduction of the diacetyliminoxyl radical into the practice of organic synthesis

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Abstract

Oxidative C–O coupling of pyrazolones with N-hydroxy compounds of different classes (N-hydroxyphthalimide, N-hydroxybenzotriazole, oximes) was achieved; both one-electron oxidants (Fe(ClO4)3, (NH4)2Ce(NO3)6) and two-electron oxidants (PhI(OAc)2, Pb(OAc)4) are applicable, and the yields reach 91%. Apparently, the coupling proceeds via the formation of N-oxyl radicals from N-hydroxy compounds. One of the N-oxyl intermediates, the diacetyliminoxyl radical, was found to be exclusively stable in solution in spite of being sterically unhindered; it was isolated from an oxidant and used as a new reagent for the synthesis and mechanism study. The products of C–O coupling of pyrazolones with N-hydroxyphthalimide can be easily transformed into aminooxy compounds, valuable substances for combinatorial chemistry.

Graphical abstract: Selective cross-dehydrogenative C–O coupling of N-hydroxy compounds with pyrazolones. Introduction of the diacetyliminoxyl radical into the practice of organic synthesis

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Publication details

The article was received on 06 Jun 2017, accepted on 17 Jul 2017 and first published on 18 Jul 2017


Article type: Research Article
DOI: 10.1039/C7QO00447H
Citation: Org. Chem. Front., 2017, Advance Article
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    Selective cross-dehydrogenative C–O coupling of N-hydroxy compounds with pyrazolones. Introduction of the diacetyliminoxyl radical into the practice of organic synthesis

    I. B. Krylov, S. A. Paveliev, B. N. Shelimov, B. V. Lokshin, I. A. Garbuzova, V. A. Tafeenko, V. V. Chernyshev, A. S. Budnikov, G. I. Nikishin and A. O. Terent'ev, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00447H

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