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Zhang, Qi; Tiefenbacher, Konrad
Journal of the American Chemical Society, 10/2013, Letnik: 135, Številka: 43Journal Article
Molecular capsules have attracted interest as simple enzyme mimetics and several examples of catalytic transformations in water-soluble metal–ligand based systems have been reported. This is not the case for hydrogen-bond based molecular capsules, which in contrast can be employed in organic solvents. We describe herein our investigations of such a system: The resorcin4arene hexamer is one of the largest hydrogen bond-based self-assembled capsules and has been studied intensively due to its ready availability. We present evidence that the capsule acts as a reasonably strong Brønsted acid (pK a approximately 5.5–6). This finding explains the capsule’s high affinity toward tertiary amines that are protonated and therefore encounter cation-π interactions inside the cavity. We were able to translate this finding into a first synthetic application: A highly substrate-selective Wittig reaction. We also report that this property renders the capsule an efficient enzyme-like catalyst for substrate selective diethyl acetal hydrolysis.
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Leto | Faktor vpliva | Izdaja | Kategorija | Razvrstitev | ||||
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JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
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Vir: Osebne bibliografije
in: SICRIS
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