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Direct C-F Bond Formation Using Photoredox Catalysis

TitleDirect C-F Bond Formation Using Photoredox Catalysis
Publication TypeJournal Article
Year of Publication2014
AuthorsRueda-Becerril, M, Mahe, O, Drouin, M, Majewski, MB, West, JG, Wolf, MO, Sammis, GM, Paquin, J-F
JournalJOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume136
Pagination2637-2641
Date PublishedFEB 12
ISSN0002-7863
Abstract

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 (MLCT)-M-3 (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.

DOI10.1021/ja412083f