Sandmeyer reaction

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The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts.[1][2][3]

The Mechanism of the Sandmeyer Reaction

An aromatic (or heterocyclic) amine will quickly react with a nitrite to form an aryl diazonium salt. This diazonium salt will decompose in the presence of copper(I) salts (such as copper(I) chloride) to form the desired aryl halide.[4][5]

Several improvements have been made to the standard procedures.[6][7]

[edit] Variations

The majority of variations of the Sandmeyer reactions consist of using various copper salts. Using cuprous cyanide as the copper salt will produce benzonitriles.[8]

The use of tetrafluoro borates which deliver the halide form for example fluorobenzene.

Substituting thiols or water for the copper salts will generate thioethers or phenols, respectively.

[edit] References

  1. ↑  Sandmeyer, T. Ber. 1884, 17, 1633.
  2. ↑  Sandmeyer, T. Ber. 1884, 17, 2650.
  3. ↑  Gattermann, L. Ber. 1890, 23, 1218.
  4. ↑  Kochi, J. K. J. Am. Chem. Soc. 1957, 79, 2942.
  5. ↑  Hodgson, H. H. Chem. Rev. 1947, 40, 251-277. (Review)
  6. ↑  Doyle, M. P. J. Org. Chem. 1977, 42, 2426.
  7. ↑  Suzuki, N. et al. Perkins Trans. I 1987, 645.
  8. ↑  Organic Syntheses, Coll. Vol. 1, p.514 (1941); Vol. 4, p.69 (1925). (Article)
  9. Organic Syntheses, Coll. Vol. 3, p.185 (1955); Vol. 24, p.22 (1944). (Article)
  10. Organic Syntheses, Coll. Vol. 4, p.160 (1963); Vol. 32, p.23 (1952). (Article)
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