148043-73-6Relevant articles and documents
Laboratory scale preparation of 4,4,5,5,5-pentafluoropentan-1-thiol: An important chain of antibreast cancer agents
Li, Xun,Provencher, Louis,Singh, Shankar M.
, p. 9141 - 9144 (1994)
Quantitative free radical addition of perfluoroethyl iodide to propargyl alcohol in the presence of sodium hydrosulfite gave E/Z-2-iodo-4,4,5,5,5-pentafluoro-2-penten-1-ols, which were converted to 4,4,5,5,5-pentafluoropentan-1-ol in one step in excellent yield by catalytic hydrogenation over platinum oxide in the presence of triethylamine. 4,4,5,5,5-Pentafluoropentan-1-thiol was obtained in good yield via modified Mitsunobu reaction of the alcohol.
Visible-Light-Mediated Iodoperfluoroalkylation of Alkenes in Flow and Its Application to the Synthesis of a Key Fulvestrant Intermediate
Rosso, Cristian,Williams, Jason D.,Filippini, Giacomo,Prato, Maurizio,Kappe, C. Oliver
supporting information, p. 5341 - 5345 (2019/07/03)
Two efficient continuous flow iodoperfluoroalkylation methods are described: using 0.05 mol % perylene diimide (PDI) photocatalyst under 450 nm irradiation or substoichiometric triethylamine under 405 nm irradiation. These methods enable dramatically elevated productivity versus batch processes. The triethylamine-mediated method is explored mechanistically and in substrate scope. The gram-scale synthesis of an active pharmaceutical ingredient side chain is also reported in flow, via a photochemical iodoperfluoroalkylation followed by hydrogenolysis.
Process for preparing pentafluoropentanol
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, (2008/06/13)
4,4,5,5,5-Pentafluoro-1-pentanol is prepared in a particularly advantageous manner from perfluoroethyl iodide by initially adding perfluoroethyl iodide in the presence of a radical initiator which does not carry any acyl groups to allyl alcohol and then hydrogenolytically dehalogenating the resulting 4,4,5,5,5-pentafluoro-2-iodo-1-pentanol in the presence of a catalyst, an acid binder and a diluent.