Palladium-catalyzed carbonylation reactions of aryl bromides at atmospheric pressure: a general system based on Xantphos.
A method for the Pd-catalyzed carbonylation of aryl bromides has been developed using Xantphos as the ligand. This method is effective for the direct synthesis of Weinreb amides, primary and secondary benzamides, and methyl esters from the corresponding aryl bromides at atmospheric pressure. In addition, a putative catalytic intermediate, (Xanphos)Pd(Br)benzoyl, was prepared and an X-ray crystal structure was obtained revealing an unusual cis-coordination mode of Xantphos in this palladium-acyl complex.
Martinelli
Joseph R
JR
Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.
Watson
Donald A
DA
Freckmann
Dominique M M
DM
Barder
Timothy E
TE
Buchwald
Stephen L
SL
D000577:Amides / Q000138:chemical synthesis* / Q000737:chemistry; D001274:Atmospheric Pressure; D002248:Carbon Monoxide / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D008024:Ligands; D008958:Models, Molecular; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010720:Phosphines / Q000737:chemistry*; D013237:Stereoisomerism; D014966:Xanthenes / Q000737:chemistry*
D000577:Amides; D004952:Esters; D006842:Hydrocarbons, Brominated; D008024:Ligands; D010720:Phosphines; D014966:Xanthenes; D010165:Palladium; D002248:Carbon Monoxide; C519861:xantphos