Larock indole synthesis using palladium complexes immobilized onto mesoporous silica

Nelly Batail, Anissa Bendjeriou-Sedjerari, Laurent Djakovitch*, Véronique Dufaud

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    27 Scopus citations

    Abstract

    Heterogeneous palladium catalysts were prepared by covalent immobilization of palladium (II) complexes of the general formula PdCl2L2 (L = P, CN) onto SBA-15 silica using a post-synthetic method. The state of the hybrid materials was characterized using a wide variety of molecular and solid-state techniques. In general, all the palladium modified solids exhibited highly ordered mesostructures while keeping the integrity of the parent molecular precursors. The catalytic performances of the materials were evaluated in the heteroannulation of 2-iodoaniline and 2-bromoaniline with triethyl(phenylethynyl)silane which showed high activities and selectivities with isolated yields in the range of 80-85%. Despite a decrease in the initial activity, quantitative conversion of iodoaniline to the expected product was observed over multiple recyclings, making these materials particularly efficient for such applications. The catalytic process was shown to be homogeneous in nature, the solid apparently serving as a "reservoir" for the metal between cycles.

    Original languageEnglish (US)
    Pages (from-to)179-187
    Number of pages9
    JournalApplied Catalysis A: General
    Volume388
    Issue number1-2
    DOIs
    StatePublished - Nov 20 2010

    Keywords

    • Heterogenous catalysis
    • Indoles
    • Larock synthesis
    • Palladium catalysts
    • SBA-15

    ASJC Scopus subject areas

    • Catalysis
    • Process Chemistry and Technology

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