Shaitanova Elena, Matoušek Václav, Herentin Tadeáš, Adamec Martin, Matyáš Robert, Klepetářová Blanka, Beier Petr
Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Flemingovo Náměstí, 2, 166 10 Prague 6, Czech Republic.
V. P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry, The National Academy of Sciences of Ukraine, Academika Kukhara Str. 1, 02094 Kyiv, Ukraine.
J Org Chem. 2023 Nov 3;88(21):14969-14977. doi: 10.1021/acs.joc.3c01346. Epub 2023 Oct 20.
A new fluorinated azidoethane─1-azido-1,1,2,2-tetrafluoroethane─was prepared in quantitative yield by the addition of an azide anion to tetrafluoroethylene in a protic medium. The title azide was shown to be thermally stable and insensitive to impact. Copper(I)-catalyzed [3 + 2] cycloaddition with alkynes afforded 4-substituted -tetrafluoroethyl-1,2,3-triazoles which underwent rhodium(II)-catalyzed transannulation with nitriles to novel -tetrafluoroethylimidazoles or the reaction with triflic acid to enamido triflates. [3 + 2] Cycloaddition of the title azide with primary amines afforded novel 5-difluoromethyl tetrazoles.
通过在质子介质中向四氟乙烯中添加叠氮阴离子，以定量产率制备了一种新的氟化叠氮乙烷——1-叠氮基-1,1,2,2-四氟乙烷。结果表明，该标题叠氮化合物热稳定且对冲击不敏感。铜（I）催化的与炔烃的[3 + 2]环加成反应生成了4-取代的四氟乙基-1,2,3-三唑，其与腈进行铑（II）催化的跨环反应生成新型的四氟乙基咪唑，或与三氟甲磺酸反应生成烯酰胺三氟甲磺酸酯。该标题叠氮化合物与伯胺的[3 + 2]环加成反应生成了新型的5-二氟甲基四唑。
