Nucleophilic reagent for preparation of alkyl methyl sulfones: J. Am. Chem. Soc., 75, 5582 (1953). Aryl methyl sulfones are formed by SNAr displacement of activated p-fluoro or p-chloro substituents from aryl aldehydes, ketones, nitriles or nitro compounds in DMSO: J. Org. Chem., 54, 4691 (1989). In the presence of CuI in DMF, displacement of non-activated iodoarenes occurs: Tetrahedron Lett., 36, 6239 (1995); see also: J. Org. Chem., 70, 2696 (2005). Under similar conditions, selective displacement of an aryl bromo substituent in the presence of an aryl fluoro can be effected.: J. Org. Chem., 70, 268 (2005). Arylboronic acids undergo displacement with the reagent under mild conditions in the presence of copper(II) acetate in DMF or DMSO; selective displacement of the boronate group from 3-bromobenzeneboronic acid is possible: Tetrahedron Lett., 45, 3233 (2004).
