Martinelli, Joseph R.
Watson, Donald A.
Freckmann, Dominique M. M.
Barder, Timothy E.
Buchwald, Stephen L.

Palladium-Catalyzed Carbonylation Reactions of Aryl Bromides at Atmospheric Pressure: A General System Based on Xantphos

“,
J. Org. Chem.
,
2008
,
73
(
18
)
,
7102-7107
.
Abstract

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, 1 degrees and 2 degrees 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.