Oxidative Fluorination of Heteroatoms Enabled by Trichloroisocyanuric Acid and Potassium Fluoride

Autor:	Yannick Kraemer, Emily Nicole Bergman, Antonio Togni, Cody Ross Pitts
Jazyk:	angličtina
Rok vydání:	2022
Předmět:	Gas-Reagent-Free Halogenation Potassium Compounds Triazines Pentafluorosulfanyl General Chemistry General Medicine Inorganic Fluorine Chemistry Oxidative Fluorination Trichloroisocyanuric Acid Catalysis Fluorides Oxidative Stress Indicators and Reagents
Zdroj:	Angewandte Chemie. International Edition, 61 (31)
ISSN:	1433-7851 1521-3773 0570-0833
Popis:	In synthetic method development, the most rewarding path is seldom a straight line. While our initial entry into pentafluorosulfanyl (SF5) chemistry did not go according to plan (due to inaccessibility of reagents such as SF5Cl at the time), a "detour" led us to establish mild and inexpensive oxidative fluorination conditions that made aryl-SF5 compound synthesis more accessible. The method involved the use of potassium fluoride and trichloroisocyanuric acid (TCICA)-a common swimming pool disinfectant-as opposed to previously employed reagents such as F-2, XeF2, HF, and Cl-2. Thereafter, curiosity led us to explore applications of TCICA/KF as a more general approach to the synthesis of fluorinated Group 15, 16, and 17 heteroatoms in organic scaffolds; this, in turn, prompted SC-XRD, VT-NMR, computational, and physical organic studies. Ultimately, it was discovered that TCICA/KF can be used to synthesize SF5Cl, enabling SF5 chemistry in an unexpected way. Angewandte Chemie. International Edition, 61 (31) ISSN:1433-7851 ISSN:1521-3773 ISSN:0570-0833
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::c4518bd4e2579a791d1790b52288978a https://hdl.handle.net/20.500.11850/556989 Zobrazit plný text záznamu Plný text