J. Vicente, I. Saura-Llamas, J. García‐López
Jan 26, 2009
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Organometallics
Abstract
Cyclometalation of 3-(2-naphthyl)-d-alanine methyl ester is achieved by reacting the corresponding hydrochloride salt and Pd(OAc)2 in a 1:1 molar ratio (acetonitrile, room temperature, 6 days). Although the chloro-bridged dimer (A) cannot be isolated in a pure form, addition of RNC to the reaction mixture affords the mononuclear derivatives (R)-[Pd{κ2(C,N)-C10H6CH2CH(CO2Me)NH2-2}Cl(CNR)] (R = tBu (1a-tBu), Xy (C6H3Me2-2,6) (1a-Xy)). Similar complexes (S)-[Pd{κ2(C,N)-C8H5N(CH2CH(CO2Me)NH2)-2}Cl(CNR)] (R = tBu (1b-tBu), Xy (1b-Xy)) are prepared from RNC and a previously reported cyclometalated derivative of l-tryptophan methyl ester, (S,S)-[Pd2{κ2(C,N)-C8H5N(CH2CH(CO2Me)NH2)-2}2(μ-Cl)2] (B). Compound 1b-Xy reacts with XyNC to give the iminoacyl complex (S)-[Pd{κ2(C,N)-C(═NXy)C8H5N(CH2CH(CO2Me)NH2)-2}Cl(CNXy)] (2b), whose crystal structure has been determined by X-ray diffraction studies. The cyclopalladated dimer B or those containing phenethylamine (C) or phentermine (D; see Chart ) reacts with RNC (R = tB...