Abstract:
(R)- and (S)-binaphthyl-2,2’-diols (BINOLs) smoothly react with pentafluoropyridine without racemization to give (R)- and (S)-2,2’- bis(tetrafluoropyridin-4-yloxy)-1,1’-binaphthyls. The 2(6)-positioned pyridine fluorine atoms can be replaced with amino moieties by reactions with amines.
Document Type:
Article
Language: English
Citation:
K. Yu. Koltunov, A. N. Chernov, “BINOL Modification via SNAr Reactions with Pentafluoropyridine”, Mendeleev Commun., 25:1 (2015), 39–40
Linking options:
https://www.mathnet.ru/eng/mendc2293
https://www.mathnet.ru/eng/mendc/v25/i1/p39
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Andrew J. Peloquin, Matthew B. Houck, Colin D. McMillen, Scott T. Iacono, William T. Pennington, “Perfluoropyridine as an Efficient, Tunable Scaffold for Bis(pyrazol‐1‐yl)pyridine Copper Complexes”, Eur J Inorg Chem, 2020:18 (2020), 1720
Alexander M. Genaev, Lyudmila N. Shchegoleva, George E. Salnikov, Andrey V. Shernyukov, Leonid A. Shundrin, Inna K. Shundrina, Zhongwei Zhu, Konstantin Yu. Koltunov, “Acid-Catalyzed Versus Thermally Induced C1–C1′ Bond Cleavage in 1,1′-Bi-2-naphthol: An Experimental and Theoretical Study”, J. Org. Chem., 84:11 (2019), 7238
William D. G. Brittain, Steven L. Cobb, “Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions”, Org. Biomol. Chem., 17:8 (2019), 2110
A. M. Genaev, G. E. Salnikov, A. V. Shernyukov, Zh. Zhu, K. Yu. Koltunov, “Enhanced enantiostability of BINOL dimethyl ether under moderate acidic conditions”, Mendeleev Commun., 28:1 (2018), 27–28
Reza Ranjbar-Karimi, Tayebeh Davodian, Hossein Mehrabi, “Reactions of pyridin-2-ol, pyridin-3-ol, and pyridin-4-ol with pentafluoro- and pentachloropyridine”, Chem Heterocycl Comp, 53:12 (2017), 1330