![N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide structure](https://static.chemtradehub.com/structs/109/109032-22-6-7c88.webp "N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide structure")
N-[2-(4-Hydroxyphenoxy)-4-nitrophenyl]methanesulfonamide
CAS Number:
109032-22-6
Molecular Formula:
C13H12N2O6S
Selective cross-dehydrogenative C–O coupling of N-hydroxy compounds with pyrazolones. Introduction of the diacetyliminoxyl radical into the practice of organic synthesis
Literature Information
Publication Date
2017-07-18
DOI
10.1039/C7QO00447H
Impact Factor
5.281
Authors
Igor B. Krylov, Stanislav A. Paveliev, Boris N. Shelimov, Boris V. Lokshin, Irina A. Garbuzova, Viktor A. Tafeenko, Gennady I. Nikishin, Alexander O. Terent'ev
View Original
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.
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Source Journal
Organic Chemistry Frontiers
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7.8
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