{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,17]],"date-time":"2026-10-17T21:33:34Z","timestamp":1792272814127,"version":"4.4.0"},"reference-count":24,"publisher":"MDPI AG","issue":"22","license":[{"start":{"date-parts":[[2020,11,19]],"date-time":"2020-11-19T00:00:00Z","timestamp":1605744000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["18-13-00173"],"award-info":[{"award-number":["18-13-00173"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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\u2013O\u00b7\u00b7\u00b7I 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.<\/jats:p>","DOI":"10.3390\/molecules25225427","type":"journal-article","created":{"date-parts":[[2020,11,19]],"date-time":"2020-11-19T10:46:26Z","timestamp":1605782786000},"page":"5427","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Fluorinated Organic Paramagnetic Building Blocks for Cross-Coupling Reactions"],"prefix":"10.3390","volume":"25","author":[{"given":"Larisa V.","family":"Politanskaya","sequence":"first","affiliation":[{"name":"N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Pavel A.","family":"Fedyushin","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2398-5271","authenticated-orcid":false,"given":"Tatyana V.","family":"Rybalova","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6918-5459","authenticated-orcid":false,"given":"Artem S.","family":"Bogomyakov","sequence":"additional","affiliation":[{"name":"International Tomography Center, Siberian Branch of Russian Academy of Sciences, 3a Institutskaya Str., 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nargiz B.","family":"Asanbaeva","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, 630090 Novosibirsk, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1540-7033","authenticated-orcid":false,"given":"Evgeny V.","family":"Tretyakov","sequence":"additional","affiliation":[{"name":"N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Ac. Lavrentiev Avenue, 630090 Novosibirsk, Russia"},{"name":"N.D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect, 47, 119991 Moscow, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2020,11,19]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Hicks, R.G. (2010). Stable Radicals: Fundamentals and Applied Aspects of Odd-Electron Compounds, John Wiley and Sons.","DOI":"10.1002\/9780470666975"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"971","DOI":"10.1070\/RC2009v078n11ABEH004093","article-title":"The chemistry of nitroxide radicals in the molecular design of magnets","volume":"78","author":"Tretyakov","year":"2009","journal-title":"Russ. Chem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Tretyakov, E., Fedyushin, P., Panteleeva, E., Gurskaya, L., Rybalova, T., Bogomyakov, A., Zaytseva, E., Kazantsev, M., Shundrina, I., and Ovcharenko, V. (2019). 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