Kiyoshi Kono

Reaction of diazonium salts with transition metals: IX. Reaction of vinyltrimethylsilane with arenediazonium tetrafluoroborates under palladium(0) catalysis☆

Arenediazonium tetrafluoroborates (ArN2BF4 where ArPh, 4-MeC6H4, 4-BrC6H4, 4-IC6H4 and 4-NO2C6H4) reacted easily with CH2CHSiMe3 at 25 δC to give ArCHCH2, (E-ArCHCHSiMe3 and Ar(Me3Si)CCH2 in excellent yields under palladium(O) catalysis. (E)-ArCHCHSiMe3 compounds were obtained predominantly and isolated in good yields by using an excess of CH2CHSiMe3 over ArN2BF4. Protodesilylation of the reaction mixture afforded styrene derivatives.

Novel transformation of arenediazonium salts to acid anhydrides under palladium catalysis

Abstract Palladium catalyzed reaction of arenediazonium salts, carbon monoxide and sodium carboxylates gave mixed anhydrides, which in turn could be converted to aromatic acid anhydrides in good yields.

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

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.