Abstract
ortho-Metallation reactions of palladium bis(hexafluoroacetylacetonate) [Pd(F 6acac) 2] have been studied by 1H and 19F NMR. N,N′-Dimethylbenzylamine produces a fluxional 1 : 1 adduct ( O-F 6acac)( O 2-F 6acac)Pd(amine) which contains a η 1 oxygen-bonded F 6acac group. The ligands benzyl methyl sulfide and 4,4′-dimethoxythiobenzophenone produce 1 : 1 intermediates of the type (C-F 6acac)( O 2-F 6acac)Pd(ligand) which contain a carbon-bonded F 6acac group. These adducts spontaneously lose hexafluoroacetylacetone and undergo cyclopalladation at room temperature. Metallation of azobenzene yields (PhNNC 6H 4)Pd(F 6acac) and the doubly ortho-metallated compound (C 6H 4NNC 6H 4)Pd 2(F 6acac) 2. Similar single metallations occur with benzylideneaniline and acetophenone oxime but thiobenzanilide gave [PhC(S)NPh] 2Pd and [PhC(S)NPh]Pd(F 6acac).
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