Cu-catalyzed Goldberg and Ullmann reactions of aryl halides using chelating N- and O-based ligands.
The following protocol can be applied in the selective cross-coupling reaction of an amine with an aryl iodide or bromide using a copper (Cu)-based catalyst to provide the corresponding N-aryl amine. The general procedure described in this text includes a detailed description of an appropriate reaction setup, two methods for assaying the crude reaction mixture (gas chromatography and thin layer chromatography) and a procedure for the isolation, purification and characterization of the anticipated product. Manipulation of the reagents can be done in the air, without the use of a glovebox; however, the cross-coupling reactions must be performed in a sealed reactor under an inert atmosphere. Three C-N bond-forming reactions are included in the protocol as representative examples of this procedure. Although the reactions can proceed in <1 h, the protocols, including workup, generally take 6-30 h to complete.
Altman
Ryan A
RA
Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, 18-490, Cambridge, Massachusetts 02139, USA.
Buchwald
Stephen L
SL
D000586:Amination; D001965:Bromides / Q000737:chemistry; D002849:Chromatography, Gas / Q000379:methods*; D002855:Chromatography, Thin Layer / Q000379:methods*; D003300:Copper / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry; D007454:Iodides / Q000737:chemistry; D008024:Ligands; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*
D001965:Bromides; D007093:Imidazoles; D007454:Iodides; D008024:Ligands; D003300:Copper; C029899:imidazole; D009584:Nitrogen; D010100:Oxygen