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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, 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.

Mechanism
The mechanism of the Wurtz–Fittig reaction has not been the subject of modern investigations. The process was once proposed to involve the combination of an alkyl and aryl radicals. Another mechanistic proposal invoked the generation of organosodium intermediates. The reaction of sodium and chlorobenzene produces triphenylene, which supports a role for radicals. == Use of other metals ==
Use of other metals
The Wurtz–Fittig reaction can be conducted using metals other than sodium. Some examples include potassium, iron, copper, and lithium. When lithium is used, the reaction occurs with appreciable yield only under ultrasound. Ultrasound is known to cleave halogen atoms from aryl and alkyl halides through a free-radical mechanism == Applications ==
Applications
The Wurtz–Fittig reaction has limited applicability because it is plagued by side reactions including rearrangements and eliminations. One example is the conversion of tetraethyl orthosilicate to the mono-tert-butoxy derivative in 40% yield as summarized in this idealized equation: : Molten sodium was used. Other organosilicon compounds synthesized using the Wurtz–Fittig reaction include silylated calixarenes and vinylsilanes. ==See also==
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