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The mercuration of 5,10,15,20-tetrakis(4-methylphenyl)porphyrin complexes M(TTP)** (2a-c; M = Ni, Pd, Pt) is described. Treatment of Ni(TTP) (2a) with mercuric acetate in refluxing benzene and subsequently with aqueous sodium chloride yields a mixture of species M(TTP-Hg n I n ) (1 &lt; n &lt; 3) from which the monomercurial, Ni(TTP-HgCl) (3a) is isolated in 35% yield after silica chromatography. A more rapid reaction occurs with mercuric trifluoroacetate in chlorobenzene. With this system, Pd(TTP-HgCl) (3b) and Pt(TTP-HgCl) (3c) along with their bis-, tris-, and tetrakis-mercurated analogs are obtained. The reaction times indicate that replacement of Ni II  by Pd II  and Pt II  progressively diminishes the rate of electrophilic attack at the porphyrin periphery, consistent with a decrease of the total density of negative charge on the porphyrin ligand in these complexes.

Metal Complexes with Tetrapyrrole Ligands, XLV. The Mercuration of Nickel(II), Palladium(II), and Platinum(II) Porphyrins