Phenanthroline Decorated by a Crown Ether as a Module for Metallorganic−Polyoxometalate Hybrid Catalysts: The Wacker Type Oxidation of Alkenes with Nitrous Oxide as Terminal Oxidant

Abstract

A 1,10-phenanthroline ligand decorated at the 5,6-position by a 15-crown-5 ether moiety was prepared. Ligation of Pd(II) at the nitrogen atom positions followed by complexation at the crown ether group of a redox active H(5)PV(2)Mo(10)O(40) polyoxometalate yielded a hybrid metallorganic-polyoxometalate complex, Pd(II)(15-crown-5-phen)Cl(2)-H(5)PV(2)Mo(10)O(40). This complex was characterized by IR, UV-vis, ESI-MS, and NMR spectroscopy and elemental analysis that all confirmed the hybrid nature of the complex. Pd(II)(15-crown-5-phen)Cl(2)-H(5)PV(2)Mo(10)O(40) was used as a catalyst for the Wacker type oxidation of 1-alkenes to yield the corresponding methylketones in essentially quantitative yields using nitrous oxide as the terminal oxidant.