Homogeneous Catalysis with Dicationic PdII Complexes: Aldol reaction of methyl isocyanoacetate with benzaldehyde

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Abstract

A series of dicationic PdII-acetonitrile complexes containing bi- and tridentate nitrogen and bidentate phosphine ligands (some of which are chiral) has been prepared as their BF4 salts. The molecular structures for two of these, [Pd(CH3CN)2(bipy)] (BF4)2 (4) and [Pd(CH3CN)((pybox)(i-Pr))] (BF4)2((S,S)-pybox(i-Pr) = 2,6-bis[(S)-4′-isopropyloxazolin-2′-yl]pyridine, 5) have been determined by X-ray diffraction. All of these complexes are shown to be effective homogeneous catalysts for the aldol-type condensation of the isonitrile, methyl isocyanoacetate, with benzaldehyde. Two isonitrile complexes, [Pd(2,2′-bipyridyl)(CNCH2COOCH3)2] (BF4)2 and [Pd((S,S)-pybox(i-Pr))(CNCH2COOCH3)] (BF4)2, have also been prepared.

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