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    Concepts for Stereoselective Acrylate Insertion
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    † Chair of Chemical Materials Science, Department of Chemistry, University of Konstanz, 78464 Konstanz, Germany
    ‡ Department of Chemistry and Biology, University of Salerno, Via Ponte Don Melillo, 84084-Fisciano (SA), Italy
    § Physical Sciences and Engineering, Kaust Catalysis Center, King Abdullah University of Science and Technology (KAUST), Thuwal 23955-6900, Saudi Arabia
    [email protected]; [email protected]
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 2013, 135, 3, 1026–1036
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    https://doi.org/10.1021/ja3101787
    Published December 20, 2012
    Copyright © 2012 American Chemical Society
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    Abstract

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    Various phosphinesulfonato ligands and the corresponding palladium complexes [{((P∧O)PdMeCl)-μ-M}n] ([{(X1-Cl)-μ-M}n], (P∧O) = κ2-P,O-Ar2PC6H4SO2O) with symmetric (Ar = 2-MeOC6H4, 2-CF3C6H4, 2,6-(MeO)2C6H3, 2,6-(iPrO)2C6H3, 2-(2′,6′-(MeO)2C6H3)C6H4) and asymmetric substituted phosphorus atoms (Ar1 = 2,6-(MeO)2C6H3, Ar2 = 2′-(2,6-(MeO)2C6H3)C6H4; Ar1 = 2,6-(MeO)2C6H3, Ar2 = 2-cHexOC6H4) were synthesized. Analyses of molecular motions and dynamics by variable temperature NMR studies and line shape analysis were performed for the free ligands and the complexes. The highest barriers of ΔG⧧ = 44–64 kJ/mol were assigned to an aryl rotation process, and the flexibility of the ligand framework was found to be a key obstacle to a more effective stereocontrol. An increase of steric bulk at the aryl substituents raises the motional barriers but diminishes insertion rates and regioselectivity. The stereoselectivity of the first and the second methyl acrylate (MA) insertion into the Pd–Me bond of in situ generated complexes X1 was investigated by NMR and DFT methods. The substitution pattern of the ligand clearly affects the first MA insertion, resulting in a stereoselectivity of up to 6:1 for complexes with an asymmetric substituted phosphorus. In the consecutive insertion, the stereoselectivity is diminished in all cases. DFT analysis of the corresponding insertion transition states revealed that a selectivity for the first insertion with asymmetric (P∧O) complexes is diminished in the consecutive insertions due to uncooperatively working enantiomorphic and chain end stereocontrol. From these observations, further concepts are developed.

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    Text, tables, figures, and CIF files giving detailed experimental procedures and analytical data, structural diagrams, selected bond lengths and angles, and crystallographic data/processing parameters for all structures. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Am. Chem. Soc. 2013, 135, 3, 1026–1036
    Click to copy citationCitation copied!
    https://doi.org/10.1021/ja3101787
    Published December 20, 2012
    Copyright © 2012 American Chemical Society
    Request reuse permissions

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