Wurtz–Fittig reaction

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Wurtz–Fittig reaction
Named after Charles Adolphe Wurtz
Wilhelm Rudolph Fittig
Reaction type Coupling reaction
Identifiers
Organic Chemistry Portal wurtz-fittig-reaction

The Wurtz–Fittig reaction is the

alkyl halides (the Wurtz reaction), Wilhelm Rudolph Fittig extended the approach to the coupling of an alkyl halide with an aryl halide.[2][3] This modification of the Wurtz reaction is considered a separate process and is named for both scientists.[1]

The Wurtz–Fittig reaction

The reaction works best for forming asymmetrical products if the halide reactants are somehow separate in their relative

organosodium bond first and thus act more effectively as a nucleophile toward the aryl halide.[4]
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.[5]

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.

3-methylbutanoic acid
after acid workup. [9][10]

Use of other metals

The Wurtz–Fittig reaction can be conducted using metals other than sodium. Some examples include potassium, iron, copper, and lithium.[11] When lithium is used, the reaction occurs with appreciable yield only under ultrasound.[12] Ultrasound is known to cleave halogen atoms from aryl and alkyl halides through a free-radical mechanism[13]

Applications

The Wurtz–Fittig reaction has limited applicability, because it is plagued by side reactions including rearrangements and eliminations.

organosilicon compounds.[14] One example is the conversion of tetraethyl orthosilicate to the mono-tert-butoxy derivative in 40% yield as summarized in this idealized equation:[15]

Si(OC2H5)4 + 2 Na + (CH3)3CCl → Si(OC2H5)3OC(CH3)3 + NaCl + C2H5ONa

Molten sodium was used.

Other

organosilicon compounds synthesized using the Wurtz–Fittig reaction include silylated calixarenes[16] and vinylsilanes.[17]

See also

References

  1. ^
    ISBN 9780470638859
    .
  2. doi:10.1002/jlac.18641310307
    .
  3. doi:10.1002/jlac.18671440308
    .
  4. ISBN 9788189473327
    .
  5. ISBN 9780470010402
    .
  6. ^
    ISSN 0009-2665
    .
  7. ^
    ISSN 0002-7863
    .
  8. ^
    ISSN 0002-7863
    .
  9. doi:10.1002/cber.190804102208
    .
  10. doi:10.1002/cber.191004302128
    .
  11. ^
    OCLC 69020965
    .
  12. ISSN 0040-4039
    .
  13. ISSN 0040-4020
    .
  14. ISSN 0368-4075
    .
  15. ISSN 0022-3263
    .
  16. PMID 17850095
    .
  17. ISSN 0039-7881
    .
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