Direct C–F Bond Formation Using Photoredox Catalysis

We have developed the first example of a photoredox catalytic method for the formation of carbon–fluorine (C–F) bonds. The mechanism has been studied using transient absorption spectroscopy and involves a key single-electron transfer from the 3MLCT (triplet metal-to-ligand charge transfer) state of...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2014-02, Vol.136 (6), p.2637-2641
Main Authors: Rueda-Becerril, Montserrat, Mahé, Olivier, Drouin, Myriam, Majewski, Marek B, West, Julian G, Wolf, Michael O, Sammis, Glenn M, Paquin, Jean-François
Format: Article
Language:English
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Summary:We have developed the first example of a photoredox catalytic method for the formation of carbon–fluorine (C–F) bonds. The mechanism has been studied using transient absorption spectroscopy and involves a key single-electron transfer from the 3MLCT (triplet metal-to-ligand charge transfer) state of Ru(bpy)3 2+ to Selectfluor. Not only does this represent a new reaction for photoredox catalysis, but the mild reaction conditions and use of visible light also make it a practical improvement over previously developed UV-mediated decarboxylative fluorinations.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja412083f