Natural Science Forum / Chemistry / Organic Synthesis / June 2006

It shouldn't be a problem.  Hydrogenation or metal reduction (like
Fe/HCl) shouldn't hit the fluorine.

C-F bonds are pretty strong, and not trivial to reduce--especially sp2 C-F
bonds.  In fact, people have had to come up with some pretty reactive
reagents to do fluorocarbon defluorination--things like titanocene or
zirconocene catalysts with Al as the ultimate reductant.  I have to believe
you should be able to find conditions to reduce Ar-NO2 but not Ar-F, but I'm
not certain what those conditions might be.  Controlled potential
electrochemistry and very mild catalytic hydrogenation are two ideas that
come to mind.  Hell, you might even get away with using Zn, Fe or Sn(II).

Eric Lucas