83235-15-8Relevant articles and documents
Tetrafluoropyridyl (TFP): a general phenol protecting group readily cleaved under mild conditions
Brittain, William D. G.,Cobb, Steven L.
supporting information, p. 2110 - 2115 (2019/02/27)
Phenols are extremely valuable building blocks in the areas of pharmaceuticals, natural products, materials and catalysts. In order to carry out modifications on phenols, the phenolic oxygen is routinely protected to prevent unwanted side reactions. Presently many of the protecting groups available can require harsh conditions, specialist equipment, expensive or air/moisture-sensitive reagents to install and remove. Here we introduce the use of the tetrafluoropyridyl (TFP) group as a general protecting group for phenols. TFP can be installed in one step with no sensitivity to water or air, and it is stable under a range of commonly employed reaction conditions including acid and base. The TFP protecting group is readily cleaved under mild conditions with quantitative conversion to the parent phenol, observed in many cases in less than 1 hour.
INTERACTION OF PENTAFLUOROPYRIDINE WITH 4-NITROPHENOL AND PENTAFLUOROPHENOL IN THE PRESENCE OF POTASSIUM FLUORIDE AND 18-CROWN-6-ETHER
Aksenov, V. V.,Vlasov, V. M.,Yakobson, G. G.
, p. 439 - 458 (2007/10/02)
The reactions of 4-nitro- and pentafluorophenols with C5F5N, 4-ArOC5F4N and 2,4-(ArO)2C5F3N (Ar = 4-NO2C6H4, C6F5) in the presence of KF and catalytic amounts of 18-crown-6-ether at various temperatures have been investigated.The leaving ability of the C6
