Fluorinated Organic Paramagnetic Building Blocks for Cross-Coupling Reactions

Fluorinated Organic Paramagnetic Building Blocks for Cross-Coupling Reactions Научная публикация

Журнал

Molecules
ISSN: 1420-3049

Вых. Данные

Год: 2020, Том: 25, Номер: 22, Номер статьи : 5427, Страниц : DOI: 10.3390/molecules25225427

Авторы

Politanskaya Larisa V. ¹ , Fedyushin Pavel A. ² , Rybalova Tatyana V. ² , Bogomyakov Artem S. ³ , Asanbaeva Nargiz B. ² , Tretyakov Evgeny V. ^4,2

Организации

1	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, 630090 Novosibirsk, Russia.
2	N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, 630090 Novosibirsk, Russia
3	International Tomography Center, Siberian Branch of Russian Academy of Sciences, 3a Institutskaya Str., 630090 Novosibirsk, Russia
4	N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect, 47, 119991 Moscow, Russia

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.

Politanskaya L.V. , Fedyushin P.A. , Rybalova T.V. , Bogomyakov A.S. , Asanbaeva N.B. , Tretyakov E.V.
Fluorinated Organic Paramagnetic Building Blocks for Cross-Coupling Reactions
Molecules. 2020. V.25. N22. 5427 . DOI: 10.3390/molecules25225427 WOS Scopus OpenAlex

Web of science:	WOS:000594125000001
Scopus:	2-s2.0-85096734850
OpenAlex:	W3103859812

БД	Цитирований
OpenAlex	16
Scopus	9
Web of science	13