Balz–Schiemann reaction

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]

The reaction is similar to the Sandmeyer reaction, which converts diazonium salts to other aryl halides.[4]

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., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=CV2P0295 ; Coll. Vol. 2: 295 
  4. ^ 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.