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An isocyanide ligand for the rapid quenching and efficient removal of copper residues after Cu/ TEMPO-catalyzed aerobic alcohol oxidation and atom transfer radical polymerization

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dc.abstract.enTransition metal catalysts play a prominent role in modern organic and polymer chemistry, enabling many transformations of academic and industrial significance. However, the use of organometallic catalysts often requires the removal of their residues from reaction products, which is particularly important in the pharmaceutical industry. Therefore, the development of efficient and economical methods for the removal of metal contamination is of critical importance. Herein, we demonstrate that commercially available 1,4-bis(3-isocyanopropyl)piperazine can be used as a highly efficient quenching agent (QA) and copper scavenger in Cu/TEMPO alcohol aerobic oxidation (Stahl oxidation) and atom transfer radical polymerization (ATRP). The addition of QA immediately terminates Cu-mediated reactions under various conditions, forming a copper complex that can be easily separated from both small molecules and macromolecules. The purification protocol for aldehydes is based on the addition of a small amount of silica gel followed by QA and filtration. The use of QA@SiO2 synthesized in situ results in products with Cu content usually below 5 ppm. Purification of polymers involves only the addition of QA in THF followed by filtration, leading to polymers with very low Cu content, even after ATRP with high catalyst loading. Furthermore, the addition of QA completely prevents oxidative alkyne–alkyne (Glaser) coupling. Although isocyanide QA shows moderate toxicity, it can be easily converted into a non-toxic compound by acid hydrolysis.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorMatyjaszewski, Krzysztof
dc.contributor.authorPiątkowski, Jakub
dc.contributor.authorRuszczyńska, Anna
dc.contributor.authorSzczepaniak, Grzegorz Bogusław
dc.contributor.authorNogaś, Wojciech
dc.contributor.authorLorandi, Francesca
dc.contributor.authorYerneni, Saigopalakrishna S.
dc.contributor.authorBulska, Ewa
dc.contributor.authorFantin, Marco
dc.contributor.authorGrela, Karol
dc.contributor.authorEnciso, Alan E.
dc.date.accessioned2024-01-24T16:43:14Z
dc.date.available2024-01-24T16:43:14Z
dc.date.copyright2020-04-15
dc.date.issued2020
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number16
dc.description.versionFINAL_PUBLISHED
dc.description.volume11
dc.identifier.doi10.1039/D0SC00623H
dc.identifier.issn2041-6520
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/100932
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofChemical Science
dc.relation.pages4251-4262
dc.rightsCC-BY-NC
dc.sciencecloudnosend
dc.titleAn isocyanide ligand for the rapid quenching and efficient removal of copper residues after Cu/ TEMPO-catalyzed aerobic alcohol oxidation and atom transfer radical polymerization
dc.typeJournalArticle
dspace.entity.typePublication