Wurtz–Fittig reaction

The Wurtz–Fittig reaction is the chemical reaction of an aryl halide, alkyl halides, and sodium metal to give substituted aromatic compounds. Following the work of Charles Adolphe Wurtz on the sodium-induced coupling of alkyl halides (the Wurtz reaction), Wilhelm Rudolph Fittig extended the approach to the coupling of an alkyl halide with an aryl halide. This modification of the Wurtz reaction is considered a separate process and is named for both scientists.

The reaction works best for forming asymmetrical products if the halide reactants are somehow separate in their relative chemical reactivities. One way to accomplish this is to form the reactants with halogens of different periods. Typically the alkyl halide is made more reactive than the aryl halide, increasing the probability that the alkyl halide will form the organosodium bond first and thus act more effectively as a nucleophile toward the aryl halide. Typically the reaction is used for the alkylation of aryl halides. With the use of ultrasound sodium reacts with some aryl halides to produce biphenyl compounds.