title: Copper-catalyzed domino halide exchange-cyanation of aryl bromides.
abstract: An efficient copper-catalyzed domino halogen exchange-cyanation procedure for aryl bromides was developed utilizing 10 mol % CuI, 20 mol % KI, 1.0 equiv of the inexpensive N,N'-dimethylethylenediamine as ligand, and 1.2 equiv of NaCN in toluene at 110 degrees C. The new method represents a significant improvement over the traditional Rosenmund-von Braun reaction: the reaction conditions are much milder, and the use of stoichiometric amounts of copper(I) cyanide and polar solvents is avoided; therefore the isolation and purification of the aromatic nitrile products is greatly simplified. In addition, the new method exhibits excellent functional group compatibility comparable to that of the analogous Pd-catalyzed cyanation methodology.
authors.affiliation: Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
authors.forename: Jacopo
authors.initials: J
authors.lastname: Zanon
authors.forename: Artis
authors.initials: A
authors.lastname: Klapars
authors.forename: Stephen L
authors.initials: SL
authors.lastname: Buchwald
mesh_terms: D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*
chemical_list: D003486:Cyanides; D006841:Hydrocarbons, Aromatic; D006842:Hydrocarbons, Brominated; D003300:Copper