Reaction of diazonium salts with transition metals. Part 13. Palladium-catalyzed carbonylative coupling of arenediazonium salts with organotin reagents to give aromatic ketones

Abstract

Palladium-catalyzed reactions of arenediazonium salts (ArN₂X; Ar = Y–Ph, Y = H, 2-, 3-, 4-Me, 2-Ph, 2-, 3-MeO, 2-, 3-, 4-Cl, 4-Br, 4-I, 2-, 3-, and 4-NO₂, X = BF₄ and PF₆) with carbon monoxide and organostannanes (R₄Sn, R = Me, Et, and Ph; RSnMe₃, R = Ph, 2-, 3-, 4-MeC₆H₄, and 4-ClC₆H₄; RSnEt₃, R = 4-NO₂C₆H₄; RSnBu₃, R = Ph) gave aromatic ketones (ArCOR) in good yields (40–95%) at room temperature.