698-51-1Relevant academic research and scientific papers
Catalyst-Free Hydrodefluorination of Perfluoroarenes with NaBH4
Schoch, Timothy D.,Mondal, Mukulesh,Weaver, Jimmie D.
supporting information, p. 1588 - 1593 (2021/03/03)
Presented is an economical means of removing fluorine from various highly fluorinated arenes using NaBH4. The procedure was adapted for different classes of perfluoroarenes. A novel isomer of an emerging class of organic dyes based on the carbazole phthalonitrile motif was succinctly synthesized in two steps from tetrafluorophthalonitrile, demonstrating the utility of the hydrodefluorination procedure. Initial exploration of the dye shows it to be photoactive and capable of facilitating contrathermodynamic styrenoid E/Z isomerization.
Polyhalogenated heterocyclic compounds. Part 42. Fluorinated nitrogen heterocycles with unusual substitution patterns
Chambers, Richard D.,Hall, Christopher W.,Hutchinson, John,Millar, Ross W.
, p. 1705 - 1713 (2007/10/03)
Reductive replacement of fluorine in 3,5-dichloro-2,4,6-trifluoropyridine 2a and pentafluoropyridine 2 using DIBAL and LAH leads to useful syntheses of fluoro and chlorofluoro pyridine derivatives. Replacement of fluorine by bromine using a mixture of HBr and AlBr3 is extremely efficient, giving excellent routes to 2,4,6-tribromo-3,5-difluoropyridine 3. Bromofluoro-pyrimidine and -quinoxaline derivatives have also been efficiently synthesised from perfluorinated precursors. Catalytic hydrogenation of bromofluoro heterocycles gives high yields of the corresponding fluorinated heterocycles. Reactions of nucleophiles with 3 gives surprising results. Soft nucleophiles, e.g. PhSNa displace bromine whereas hard nucleophiles, e.g. MeONa, displace fluorine. British Crown Copyright 1998, Defence Evaluation and Research Agency. Published by the Royal Society of Chemistry with the permission of the controller of Her Britannic Majesty's Stationery Office.
