Supramolecular Pd@methioine-EDTA-chitosan nanocomposite: an effective and recyclable bio-based and eco-friendly catalyst for the green Heck cross-coupling reaction under mild conditions

Abstract

Supramolecular palladium(II) supported on modified chitosan by DL-methionine using an ethylenediaminetetraacetic acid linker (Pd@MET-EDTA-CS) was designed and prepared through a simple procedure. The structure of this novel supramolecular nanocomposite was characterized by different spectroscopic, microscopic and analytical techniques including FTIR, EDX, XRD, FESEM, TGA, DRS, TEM, AA, and BET. The obtained bio-based nanomaterial was successfully investigated, as a highly efficient and green heterogeneous catalyst, in the Heck cross-coupling reaction (HCR) for the synthesis of various valuable biologically active cinnamic acid ester derivatives from the corresponding aryl halides using several acrylates. Indeed, aryl halides containing I or Br survived very well under optimized conditions to afford the corresponding products compared to the substrates with Cl. The prepared Pd@MET-EDTA-CS nanocatalyst promoted the HCR in high to excellent yields and short reaction times with minimum Pd loading (0.0027 mol%) on its structure as well as without any leaching occurring during the process. The recovery of the catalyst was performed by simple filtration and the catalytic activity remained approximately constant after five runs for the model reaction.