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. Author manuscript; available in PMC: 2012 May 26.
Published in final edited form as: Nature. 2011 May 26;473(7348):470–477. doi: 10.1038/nature10108

Figure 3. Electrophilic silver-catalyzed Ar–F bond-forming reaction.

Figure 3

a, The first silver-catalyzed Ar–F bond-forming reaction. Aryl stannane derivatives (7) were fluorinated using 5 mol% of Ag2O as catalyst and the electrophilic fluorination reagent F-TEDA-PF6 (8). The reaction was applied to late-stage fluorination of complex small molecules, including taxol (9), strychnine (10), and rifamycin (11) derivatives. b, The proposed mechanism of the silver-catalyzed electrophilic fluorination includes three elementary steps: transmetallation, oxidation by an electrophilic fluorination reagent, and C–F reductive elimination. (Bu: butyl).