Sandmeyer Reaction (Gattermann Reaction) (Körner-Contardi Reaction)

T. Sandmeyer, Ber. 17, 1633, 2650 (1884); L. Gattermann, Ber. 23, 1218 (1890); G. Körner, A. Contardi, Atti Accad. Naz. Lincei 23 II, 464 (1914), C.A. 9, 1478 (1915).

Substitution of diazonium groups in aromatic compounds by halo or cyano groups in the presence of cuprous salts (Sandmeyer reaction), copper powder and hydrochloric or hydrobromic acid (Gattermann reaction) or cupric salts (Körner-Contardi reaction):

Early reviews: H. H. Hodgson, Chem. Rev. 40, 251-277 (1947); W. A. Coudrey, D. S. Davies, Q. Rev. Chem. Soc. 6, 358-379 (1952); A. Roedig, Houben-Weyl 5/4, 438 (1960); R. Stroh, ibid. 5/3, 846 (1962). Direct conversion of aryl amines to aryl halides: M. P. Doyle, J. Org. Chem. 42, 2426 (1977). Mechanistic studies: J. K. Kochi, J. Am. Chem. Soc. 79, 2942 (1957); C. Galli, J. Chem. Soc. Perkin Trans. 2 1984, 897. Synthetic application: C. Corral et al., Heterocycles 23, 1431 (1985). Improved methodology: N. Suzuki et al., J. Chem. Soc. Perkin Trans. 1 1987, 645; A. P. Krapcho, S. N. Haydar, Heterocycl. Commun. 4, 291 (1998).