Aromatic Fluorination

ArOSO₂CF₃  +  CsF  →  ArF

A recent Science paper (published on the web) from Stephen Buchwald and his group describes a system for generating aromatic fluorides by palladium catalysed displacement of triflates using cesium fluoride.  The key is the bulky ligand (shown below) used to activate the catalyst.  Those people who attended The 19th International Conference on Organic Process Research and Development, held in Fort Lauderdale FL in April 2009 will remember from Vladimir Grushin’s excellent presentation how much work has gone in to trying to find a catalytic system to effect this type of transformation.

D.A. Watson, M. Su, G. Teveroskiy, Y. Zhang, J. Garcia-Fortanet, T. Kinzel, and S.L. Buchwald, Science, 2009, 10.1126/science.1178239.