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Fluorinated Organic Paramagnetic Building Blocks for Cross-Coupling Reactions.


ABSTRACT: New stable polyfluorinated nitroxide radicals for use in cross-coupling reactions, namely, N-tert-butyl-N-oxyamino-2,3,5,6-tetrafluoro-4-iodobenzene and N-tert-butyl-N-oxyamino-2,3,5,6-tetrafluoro-4-ethynylbenzene, were prepared from perfluoroiodobenzene. The reaction of the polyfluoro derivative with tert-butylamine under autoclaving conditions leading to the formation of N-tert-butyl-2,3,5,6-tetrafluoro-4-iodoaniline proved to be the key stage of the whole process. The fluorinated tert-butyl iodophenyl nitroxide was found to form in a solid state via N-O···I halogen bonds, a one-dimensional assembly of the radicals. The acceptor role of the nitroxide group in the halogen bonding changes to a donor role when the nitroxide reacts with Cu(hfac)2. In the last case, zero-dimensional assembly prevails, giving a three-spin complex with axial coordinated nitroxide groups and, as a consequence, causing ferromagnetic intramolecular exchange interactions between Cu(II) and radical spins.

SUBMITTER: Politanskaya LV 

PROVIDER: S-EPMC7699513 | biostudies-literature | 2020 Nov

REPOSITORIES: biostudies-literature

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Fluorinated Organic Paramagnetic Building Blocks for Cross-Coupling Reactions.

Politanskaya Larisa V LV   Fedyushin Pavel A PA   Rybalova Tatyana V TV   Bogomyakov Artem S AS   Asanbaeva Nargiz B NB   Tretyakov Evgeny V EV  

Molecules (Basel, Switzerland) 20201119 22


New stable polyfluorinated nitroxide radicals for use in cross-coupling reactions, namely, <i>N</i>-<i>tert</i>-butyl-<i>N</i>-oxyamino-2,3,5,6-tetrafluoro-4-iodobenzene and <i>N</i>-<i>tert</i>-butyl-<i>N</i>-oxyamino-2,3,5,6-tetrafluoro-4-ethynylbenzene, were prepared from perfluoroiodobenzene. The reaction of the polyfluoro derivative with <i>tert</i>-butylamine under autoclaving conditions leading to the formation of <i>N</i>-<i>tert</i>-butyl-2,3,5,6-tetrafluoro-4-iodoaniline proved to be t  ...[more]

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