Palladium complexes of a chiral P,C-chelating phosphino-(sulfinylmethyl)phosphonium ylide ligand |
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Authors: | Remigiusz Zurawinski Marian Mikolajczyk |
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Affiliation: | a Center of Molecular and Macromolecular Studies, Department of Heteroorganic Chemistry, Polish Academy of Sciences, Sienkiewicza 112, 90-363 Lodz, Poland b Laboratoire de Chimie de Coordination du CNRS, 205 Route de Narbonne, 31077 Toulouse Cedex 4, France |
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Abstract: | A new type of phosphino-phosphonium ylide ligand bearing a chiral sulfinyl center affords a P,C-chelated palladium(II) complex with a resolved asymmetric ylidic carbon atom. According to 31P NMR analysis of the crude material, the diastereoselectivity of the complexation at room temperature is ca. 7:1. In the crystal state, an X-ray diffraction analysis of one epimer reveals a quasi C2-symmetric chloro-bridged dinuclear structure, where the (S) configuration of the sulfur atom induces a (S) configuration of the ylidic carbon atom. A in situ Pd(0) catalyst generated from the phosphino-ylide and Pd(PPh3)4 promotes allylic substitution of 3-acetoxy-1,3-diphenylpropene by sodium malonate in 70% yield and 5% e.e. |
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Keywords: | Chiral palladium complexes Ylide complexes Phosphoniophosphines Chiral sulfoxides Allylic substitution |
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