FLUOROCROSS · A Catalytic Method to Form Carbon–Carbon Bonds by Coupling Two Carbon–Fluorine Bonds.

A Catalytic Method to Form Carbon–Carbon Bonds by Coupling Two Carbon–Fluorine Bonds.

The biaryl motif contains two benzene rings joined by a carbon–carbon bond and is an established chemical building block. In recent years, there has been keen interest in biaryls containing fluorine atoms. The combination of a rigid, potentially planar, biaryl group and electronegative fluorine atom(s) engenders key benefits to organic molecules designed for use in liquid crystal displays or as the active ingredient in pharmaceuticals or agrochemicals. Biaryls are typically synthesized by coupling of an organometallic reagent with an aryl halide, a synthetic method that resulted in the 2010 Nobel Prize in chemistry. Despite wide-spread adoption of this approach, only recently have catalysts been developed that allow the cross-coupling of organometallics with carbon–fluorine bonds; most methods rely on the use of substrates containing weaker carbon–bromine or carbon–iodine bonds. The direct coupling of two different fluorinated substrates by a reaction which breaks two carbon–fluorine bonds is unknown. If such a reaction could be developed it would open up the use of inexpensive fluorocarbons in synthesis.

Data: CORDIS, © European Union