Wurtz–Fittig reaction

The Wurtz–Fittig reaction is the chemical reaction of aryl halides with alkyl halides and sodium metal in the presence of dry ether to give substituted aromatic compounds. The reaction is named after Charles-Adolphe Wurtz, who discovered in 1855 a similar reaction between two alkyl halides (Wurtz reaction), and Rudolph Fittig, who discovered that also aryl halides undergo this reaction.

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; however, with the use of ultrasound the reaction can also be made useful for the production of biphenyl compounds of type Ph–Ph.