1534-53-8Relevant academic research and scientific papers
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.
Visible light-promoted metal-free C-H activation: Diarylketone-catalyzed selective benzylic mono- and difluorination
Xia, Ji-Bao,Zhu, Chen,Chen, Chuo
supporting information, p. 17494 - 17500 (2014/01/06)
We report herein an operationally simple method for the direct conversion of benzylic C-H groups to C-F. We show that visible light can activate diarylketones to abstract a benzylic hydrogen atom selectively. Adding a fluorine radical donor yields the benzylic fluoride and regenerates the catalyst. The selective formation of mono- and difluorination products can be achieved by catalyst control. 9-Fluorenone catalyzes benzylic C-H monofluorination, while xanthone catalyzes benzylic C-H difluorination. The scope and efficiency of this new C-H fluorination method are significantly better than those of the existing methods. This is also the first report of selective C-H gem-difluorination.
