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. 2009 Aug 15;65(33):6576-6583.
doi: 10.1016/j.tet.2009.04.096.

An Efficient System For the Pd-Catalyzed Cross-Coupling of Amides and Aryl Chlorides

Brett P Fors  1 , Karin Dooleweerdt, Qingle Zeng, Stephen L Buchwald
Affiliations

An Efficient System For the Pd-Catalyzed Cross-Coupling of Amides and Aryl Chlorides

Brett P Fors et al. Tetrahedron. .

Abstract

A catalyst based on a new biarylphosphine ligand (3) for the Pd-catalyzed cross-coupling reactions of amides and aryl chlorides is described. This system shows the highest turnover frequencies reported to date for these reactions, especially for aryl chloride substrates bearing an ortho substituent. An array of amides and aryl chlorides were successfully reacted in good to excellent yields.

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Figures

Figure 1
Figure 1
Biarylphosphine ligands.
Figure 2
Figure 2
Pd(II) oxidative addition complex based on ligand 1.
Figure 3
Figure 3
Results observed for the coupling of acetamide and 2-chlorotoluene with various ligands.
See this image and copyright information in PMC

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