1068560-20-2Relevant academic research and scientific papers
Nucleophilic fluorination of triflates by tetrabutylammonium bifluoride
Kim, Kyu-Young,Bong, Chan Kim,Hee, Bong Lee,Shin, Hyunik
, p. 8106 - 8108 (2008)
(Chemical Equation Presented) Careful examination of nucleophilicity, basicity, and leaving group ability led us to discover the nucleophilic fluorination of triflates by weakly basic tetrabutylammonium bifluoride, which provides excellent yields with minimal formation of elimination-derived side products. Primary hydroxyl groups as well as secondary hydroxyl groups in acyclic chains or in five-membered rings are excellent substrates, whereas benzylic and aldol-type secondary hydroxyl groups give poor yields as a result of the instability of their triflates.
Cis-specific hydrofluorination of alkenylarenes under palladium catalysis through an ionic pathway
Emer, Enrico,Pfeifer, Lukas,Brown, John M.,Gouverneur, Veronique
supporting information, p. 4181 - 4185 (2014/05/06)
This paper describes the hydrofluorination of alkenes through sequential H- and F+ addition under palladium catalysis. The reaction is cis specific, thus providing access to benzylic fluorides. The mechanism of this reaction involves an ionic pathway and is distinct from known hydrofluorinations involving radical intermediates. The first catalytic enantioselective hydrofluorination is also disclosed. See attached PdF: A series of benzylic fluorides was prepared by hydrofluorination which proceeds through a PdII/IV catalytic manifold. The method is mechanistically distinct from previously reported radical hydrofluorination, and is characterized by its clean regioselectivity and unique cis stereospecificity. The first example of enantioselective net HF addition onto 2-vinylnaphthalene is also disclosed.
