Easing in Fluorine

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Science  03 Sep 2010:
Vol. 329, Issue 5996, pp. 1129
DOI: 10.1126/science.329.5996.1129-d

Fluorine is proving an increasingly useful substituent in pharmaceutical compounds (both for its intramolecular inductive effects and its intermolecular docking tendencies), but its introduction often remains a synthetic challenge. Tang et al. now show that a silver catalyst can transfer fluorine from a common electrophilic amine-based source to tin-bearing carbons in a wide range of aryl structures under mild heating. The authors had previously demonstrated a similar reaction using excess silver, and then discovered that adding bicarbonate was the key to enabling catalysis: The base intercepts an otherwise disruptive acid by-product. The catalyst tolerates numerous functional groups, as showcased by the authors through fluorination of structurally complex molecules such as strychnine. Preliminary mechanistic studies implicate multiple silver centers in one or more steps of the cycle. At the same time, the catalyst appears to be fully homogeneous, a rare circumstance for silver, which in redox catalysis is more often used heterogeneously.

J. Am. Chem. Soc. 132, 10.1021/ja105834t (2010).

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