Abstract
A low-waste, time-economical, and scalable semiheterogeneous purification protocol for the removal of ruthenium residues from olefin metathesis (OM) reactions has been developed. It is based on the non-covalent immobilization of the commercially available isocyanide 1,4-bis(3-isocyanopropyl)piperazine (QA) on unmodified silica gel. The use of the heterogeneous scavenger QA@SiO2 synthesized in situ during the purification process was shown to yield OM products with metal contamination usually below 5 ppm. Furthermore, the new purification protocol was effective on a gram scale in the ring-closing OM of an intermediate in the synthesis of cathepsin K inhibitors, leading to a product containing only 0.29 ppm Ru. Finally, QA was used in an aqueous medium and reduced the metal contamination from 9977 to 21 ppm.
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