Balz–Schiemann reaction

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The Schiemann reaction (also called the Balz–Schiemann reaction) is a chemical reaction in which anilines (1) are transformed to aryl fluorides (3) via diazonium fluoroborates (2).[1][2] Named after the German chemists Günther Schiemann and Günther Balz, this reaction is the preferred route to fluorobenzene and some related derivatives,[3] including 4-fluorobenzoic acid.[4]

The reaction is similar to the Sandmeyer reaction, which converts diazonium salts to other aryl halides.[5]

References

  1. ↑ Günther Balz, Günther Schiemann (1927). "Über aromatische Fluorverbindungen, I.: Ein neues Verfahren zu ihrer Darstellung". Ber. 5 (60): 1186–1190. doi:10.1002/cber.19270600539. 
  2. ↑ Roe, A. Org. React. 1949, 5, 193. (Review)
  3. ↑ Flood, D. T. (1943), "Fluorobenzene", Org. Synth. ; Coll. Vol. 2: 295 
  4. ↑ G. Schiemann; W. Winkelmüller (1943), "p-Fluorobenzoic Acid", Org. Synth. ; Coll. Vol. 2: 299 
  5. ↑ Swain, C. G.; Rogers, R. J. (1975). "Mechanism of formation of aryl fluorides from arenediazonium fluoborates". J. Am. Chem. Soc. 97: 799–800. doi:10.1021/ja00837a019. 
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