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Inclusion complexes of cucurbit[n]urils (n = 7, 8) with η5‐cyclopentadienyl methyl tricarbonyl molybdenum(II) and their use in epoxidation catalysis

Neves, Patrícia ; Gomes, Ana C. ; Monteiro, Rodrigo P. ; Santos, Mirela J. ; Valente, Anabela A. ; Lopes, André D. ; Gonçalves, Isabel S. ; Pillinger, Martyn

Applied organometallic chemistry, 2024-05, Vol.38 (5), p.n/a [Periódico revisado por pares]

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  • Título:
    Inclusion complexes of cucurbit[n]urils (n = 7, 8) with η5‐cyclopentadienyl methyl tricarbonyl molybdenum(II) and their use in epoxidation catalysis
  • Autor: Neves, Patrícia ; Gomes, Ana C. ; Monteiro, Rodrigo P. ; Santos, Mirela J. ; Valente, Anabela A. ; Lopes, André D. ; Gonçalves, Isabel S. ; Pillinger, Martyn
  • Assuntos: carbonyl complexes ; cucurbiturils ; inclusion compounds ; molybdenum ; olefin epoxidation
  • É parte de: Applied organometallic chemistry, 2024-05, Vol.38 (5), p.n/a
  • Descrição: There are very few known examples of supramolecular compounds comprising molybdenum species hosted inside the portals/cavities of cucurbit[n]urils (CBn). In this work, CB7 and CB8 macrocycles have been studied as hosts for the carbonyl complex [CpMo(CO)3Me] (1) (Cp = η5‐C5H5). Compounds were isolated in the solid state and characterized as genuine 1:1 inclusion complexes (1@CBn) by elemental and thermogravimetric analyses, powder X‐ray diffraction, scanning electron microscopy, 13C{1H} cross‐polarization magic‐angle spinning NMR, FT‐IR, Raman, and diffuse reflectance UV–Vis spectroscopies. The host–guest structures can act as supramolecular precatalysts for olefin epoxidation. Based on the model reaction of cis‐cyclooctene with hydroperoxide oxidants (tert‐butylhydroperoxide or hydrogen peroxide), the structural features of 1@CBn as well as the operating conditions influence the catalytic process. The metal species in 1@CBn undergo oxidative decarbonylation in situ, giving oxidized metal species that are catalytically active for olefin epoxidation. The type of oxidant and solvent influences the catalytic activity and stability. 1@CB8 was more stable than 1@CB7 with regard to catalyst recycling and reuse. Based on the substrate scope investigation, for relatively large olefins, such as the fatty acid methyl ester methyl oleate, the size of the macrocyclic host may be a determining factor for catalytic activity. Supramolecular precatalysts comprising cucurbituril hosts and a cyclopentadienyl molybdenum carbonyl guest were prepared and characterized in the solid state to confirm inclusion complexation. The performance and recyclability of the compounds for heterogeneous olefin epoxidation is dependent on the operating conditions and the structural features (macrocycle size) of the host.
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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