1. Zach Niemeyer, Justin Salvant University of Utah
Lipitor
Aryl Fluorination
Zach Niemeyer, Justin Salvant
University of Utah

2. Aryl Fluorination Mechanism:
Overview: Aryl fluorines are present in two of the top 10 grossing drugs (Lipitor and Reserdal). The C-F bond is uniquely strong and prevents facile metabolism, giving these compounds longer T1/2 in vivo. The generalized mechanism for electrophilic aryl fluorination proceeds through a high valent metal species.
Mechanism:
Wiki Page:

3. Aryl Fluorination
Overview: Aryl fluorines are present in two of the top 10 grossing drugs (Lipitor and Reserdal). The C-F bond is uniquely strong and prevents facile metabolism, giving these compounds longer T1/2 in vivo. The generalized mechanism for electrophilic aryl fluorination proceeds through a high valent metal species.
Early Examples
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4. Examples
REFERENCES: Tang, P.; Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2010, Lee, E.; Kamlet, A.; Powers, D.; Neumann, C.; Boursalian, G.; Furuya, T.; Choi, D.; Hooker, J.; Ritter, T. Science 2011,

5. Problems
Assuming the catalytic cycle shown, predict the product formed upon the
addition of exogenous water:
What is the role of NaOTf in the reaction below? (Hint: Ag2O is only partially soluble)
References: Tang, P.; Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2010,

6. Contributed by: Zach Niemeyer, Justin Salvant (Undergraduates)
University of Utah, 2013