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Palladium-catalyzed arylation of (di)azinyl aldoxime ethers by aryl iodides: stereoselective synthesis of unsymmetrical (E)-(di)azinylaryl ketoxime ethers.

The first example of direct arylation of (di)azinyl aldoxime ethers by aryl iodides is reported. The reaction produces, in a single step, a variety of geometrically pure unsymmetrical (E)-(di)azinylaryl ketoxime ethers, a class of nitrogenated motifs that have found wide applications in medicinal and organic chemistry but are difficult to access using conventional procedure. The utility of the method is further illustrated in a formal synthesis of the Merck melanin-concentrating hormone 1 receptor antagonist.